CA1222747A - Herbicidal sulfonamides - Google Patents

Abstract

Title BA-8591A
HERBICIDAL SULFONAMIDES
Abstract of the Disclosure This invention relates to certain herbicidally active sulfonamide compounds, suitable agricultural composition thereof and a method for their use as general and/or selective preemergence or postemergence herbicides or plant growth regulants. More specifically the compounds are of the formula:

I
wherein W1 is O or S;
R7 is H or CH3:
R is H, C1-C4 alkyl optionally substituted with 0-3 halogen atoms selected from 1-3 F, 1-2 Cl or 1 Br, C1-C4 alkylthio, C1-C4 alkoxy, CH2OCH3, CH2CH2OCH3 or CH2SCH3;

R1 is H, halogen, C1-C3 alkyl, C1-C3 haloalkyl, nitro, C1-C3 alkoxy, di(C1-C2)alkylamino-sulfamoyl, C1-C3 alkylthio, C1-C3 haloalkoxy, C1-C3 haloalkylthio, cyano, C1-C3 alkylsul-finyl, C1-C3 alkylsulfonyl, C2-C3 alkoxycar-bonyl, CH2OCH3, CH2SCH3 or CH2CN;
R2 is H or CH3:
W is O, 6 or NR3;
R3 is H or CH3;

A is X is H, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 halo-alkoxy, C1-C3 haloalkyl, C1-C3 haloalkylthio, C1-C3 alkylthio, halogen, C2-C3 alkoxyalkyl, C2-C3 alkoxyalkoxy, amino, C1-C3 alkylamino or di (C1-C3) alkylamino;
Y is H, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 halo-alkoxy, C1-C3 haloalkylthio, C1-C3 alkylthio, halogen, C2-C3 alkoxyalkyl, C2-C3 alkoxyalkoxy.
amino, C1-C3 alkylamino, di(C1-C3)alkylamino, C3 alkenyloxy, C3 alkynyloxy, C2-C3 alkynyl, C2-C3 alkylthioalkyl, C2-C3 alkylsulfinyl-alkyl, C2-C3 alkylsulfonylalkyi, C1-C3 halo-alkyl, cyclopropyl, C(O)R4, , or N(OCH3)CH3;
m is 2 or 3;
L1 and L2 are independently O or S;
R4 is H or CH3;
R5 and R6 are independently C1-C2 alkyl;
Z is CH or N;
Y1 is O or CH2;
X1 is CH3, OCH3, OC2H5 or OCF2H;
Y2 is H or CH3;
X2 is CH3, OCH3 or SCH3;
Y3 is CH3, C2H5 or CH2CF3;
X3 is CH3 or OCH3;
X4 is CH3, OCH3, OC2H5, CH2OCH3 or Cl; and Y4 is CH3, OCH3, OC2H5 or Cl;
and their agriculturally suitable salts;
provided that a) when W1 is S, then R7 is H, A is A-1 and Y is CH, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3, CH(OCH3)2 or ;
b) when X or Y is OCF2H, then Z is CH;
c) when X is F, Cl, Br or I, then Z is CH and Y
is OCH3, OC2H5, OCF2H, NH2, NHCH3, N(OCH3)CH3 or N(CH3)2;
d) when R1 is di(C1-C2)alkylaminoriulfamoyl or C2-C3 alkoxycarbonyl, then Q is Q-1 and R1 is in the 5-position; or Q is Q-2 and R1 is in the 6-position; and e) when the total number of carbon atoms of X
and Y is greater than four, then the number of carbon atoms of R is less than or equal to two and the number of carbon atoms of R1 is less than or equal to two.

Description

~2~ 74~

Titl~ BA-8591-A
HERBICIDAL SULFONAMIDES
BACKGROUND OF THE INVENTION
This invention relates to herbicidally active sulfonamide compounds, 6uitable agricultural composi-tions thereof and a method for their u6e as a pre- or postemergence herbicide and/or plant growth regulant.
New compound~ effective for controllinq the growth of undesired vegetation are in constant demand.
In the mo6t common 6ituation, such compound6 are sought to selectively control the growth of weeds in u6eful CrOp6 6uch as cotton, rice, corn, wheat and soybaans, to name a few. Unchecked weed growth in 6uch crop6 can cause significant lo~se6, reducing profit to the farmer and increasing co ts to the con6umer. In other situations, herbicide6 are desired which will control all plant growth. Examples of areas in which complete control of all vegetation i6 de6ired are areas around fuel ~torage tanks, ammunition depots and industrial storage areas. There are many produc~s commercially available for ~hese purpose6, but the 6earch continues for produce~ which are more effective, les6 c06tly and environmentally safe.
A number of different types of N-[(heterocyclic)-aminoca~bonyl]aryl - and heeeroarylsulfonamides are known as herbicide6.
U.S. 4,391,~27 discloses herbicidal sulfonamide~
of formula at 0 ~ ~
R9~ S02NHCN~ <Z

where ~ is O or S.

~7~

European Patene ~pplication (EP-~) No. 70,698, published January 26,1983, describe6 herbicidal sulfonamides of formula ~4 N I
~0\
N R ~5 N
~3 ~2 where R2 i~ H, Cl-C3 alkyl or S02C6H5.

EP-A 79,683, published May 25, 1983, discloses herbicidal sulfonamide6 of formula 1 o N

~ N ~
Y
where Q i8 0, S or SO2.

The current population explosion and concomitant world food and fiber shortage demand improvement in the efficiency of producing the6e crops. Preventing or mini~izing 1066 of valuable crops by killing or inhibiting the growth of unde~ired vegetation is one way of improving this efficiency. Even though there are a wide variety of products useful for killing and inhibiting growth of undesired vegetation the need still exi6t6 for more effective herbicides.

~7 Su~mar~of the~ l~vention Thi~ invention relates to novel compound6 of Formula I, 6uitable agrieultuIal composition6 con-taining them and their method of u~e a6 general and/or selective preemergence andtor postemergence herbicide~
and/or plant growth regulants. In accordance with the invention the compounds of Formula I are Wl Qso2NHcNA

I
wherein lS Q i~ ~1 ~ R , ~l ~ R

Q~ -2 ~2 ~r R~ ~ 2 ;
H

Wl i8 0 or S;
R7 is H or CH3;
R is H, Cl-C4 alkyl optionally sub6tituted with 0-3 halogen atoms selected from 1-3 F, 1-2 Cl or 1 Br, Cl-C4 alkylthio, Cl-C4 alkoxy,

2 3' 2 2 3 2 H3;

Rl i8 H, halogen, Cl-C3 alkyl, Cl-C3 haloalkyl, ni~o~ Cl-C3 alkoxy, di(Cl-C2)alkylamino-sulfamoyl, Cl-C3 alkylthio, Cl-C3 haloalkoxy, Cl-C3 haloalkylthio, cyano, Cl C3 alkyl6ul-finyl, Cl-C3 alkyl6ulfonyl, C2-C3 alkoxycar-bonyl, CH20CH3, CH2SCH3 o~ CH2CN;
R2 is H or CH3;
W i~ 0, S or NR3;
R3 i~ H or CH3;

A i~

A-l A-2 -3 A-4 , H~C ~ o~

~ i~ H, Cl-C~ alkyl, Cl-C3 alkoxy, Cl-C3 halo-alkoxy, Cl~C3 haloalkyl, Cl-C3 haloalkylthio, Cl-C3 alkylthio, halogen, C2-C3 alkoxyalkyl, C2-C3 alkoxyalkoxy, amino, Cl-C3 alkylamino o~ di(Cl-C3)alkylamino;
Y i8 H, Cl-C3 alkyl, Cl-C3 alkoxy~ Cl-C3 halo-alkoxy, Cl-C3 haloalkyl~hio, Cl-C3 alkylthio, halogen, C2-C3 alkoxyalkyl. C2-C3 alkoxyalkoxy, amino, Cl-C3 alkylamino, di(Cl-C`3)alkylamino, C3 alkenyloxy, C3 alkynyloxy, C2-C3 alkynyl, C2-C3 alkylthioalkyl, C2-C3 alkyl~ulfinyl-alkyl, C2-C3 alkyl~ulfonylalkyl, Cl-C3 halo-alkyl, cyclopropyl, C(O)R4, -C 1 5 , R~ 2 6 ,L~ ~ CH3 ~`L ~ 2)m' ~q ~ or N(OCH3)CH3;

i5 2 or 3;
Ll and L2 are independenely O or S:
R4 i6 H or C~3;
R5 and R6 are independently Cl-C2 alkyl:
Z is CH or N;
Yl is O or CH2;
~ CH3, OCH3, OC2H5 or OCF2H;
Y2 is H or CH3;
lS ~2 is CH3, OCH3 or SCH3;
Y3 is CH3~ ~2~5 or CH2CF3;

3 3 3;

4 3, OCH3. OC2H5, CH2OCH3 or Cl; and 4 3' 3' 2 5 and their agriculturally suitable salts:
provided that a) when Wl is S, then R7 is H, A is A-l and Y is 3 3' C2H5' CH2CH3- C2H5. CF3, SCH3, OCH2CH=CH2. OCH2C-CH, OCH2CH2OCH~. CH(OCH3)2 or CH ~ ;
\O J
b) when ~ or Y i~ OCF2H, then Z i6 CH;
c) when ~ i6 F, Cl, Bc or I, then Z i~ CH and Y
is OCH3. OC2H5. OCF2H- NH2' NHCH3- ( 3 3 or N(CH312;
d) when Rl i~ di(Cl-C2]alkylaminosulfa~oyl or C2-C3 alkoxycarbonyl, rhen Q is Q-l and Rl is in the 5-po6ition; or Q i s Q-2 ~nd Rl is in the 6-position; and ~22~79~

e) when the total number of carbon atoms of ~
and Y i greater than four, then the number of carbon atoms of R i6 le6s than or equal to two, and the number of carbon a~om6 of R
i6 le~s than or ~qual ~o two.
In the above defini~ions, ~he term "alkyl", u6ed either alone or in compound word~ ~uch a~ "alkylthio"
or "haloalkyl", denote6 ~traight chain or branched alkyl, e.g. methyl, ethyl, n-propyl oc i60propyl.
Alkoxy denotes methoxy, ethoxy, n-propoxy or i60propoxy.
Alkenyl denotes 6traight chain or branched alkene~, e.g. l-propenyl, 2-propenyl or 3-propenyl.
Alkynyl denotes l-propynyl or 2-propynyl.
The term "halogen", either alone or in compound words 6uch as "haloalkyl", denote6 fluorine, chlorine, bromine or iodine.
Alkoxycarbonyl denote~ methoxycarbonyl or ethoxyca~bonyl.
Alkylsulfonyl denote6 methyl6ulfonyl, ethyl-sulfonyl and the different propylsulfonyl i60mer6.
Alkylthio, alkyl~ulfinyl, alkylamino, etc. are defined in an analogou6 manner.
In ter~s such a6 C~-C3 alkylthioalkyl, the speci-fied number of carbon atoms i6 meant to define the total number of carbon atom~ in that substituent group. For example, C2-C3 alkylthioalkyl would desi~nate CH2SCH3, CH2SC2H5, CH2CH2SCH3 or CH(CH3~SCH3, and C2-C5 alkoxy-alkoxy would represent OCH20CH3 through O(CH2)40CH3 or OCH20(CH2)3CH3 and the various structural isomers embraced therein.
The preferred compound6 for rea60n6 of greater herbicidal efficacy and/or increa6ed ease of ~ynthe6i~
are:

~2~

1) Compound~ of Formula I where ~ 0, R7 i~ H, ~ i~ CH3, OCH3, OC2H5, halogen, OCF2H, CH~F, OCH2CH2F, OCH2CH~2, OCH2CF3 or CF3, and Y is H, CH3, OCH3, 0C2H5, CH20CH3, NHCH3, N(OCH3)CH3, ~(CH ) ~ ~2Hs~ CF3~ SCH3, OCH2c~ C~2, 2 C--CH, C--CCH3, CH20C2H5, OCH2CH~OOE 3, 2 3 ~ ) 4~ ,C~ a ' C~L ~C~2)m~

OCF2H, SCF2H or cyclopropyl:
2) Compound6 of Preferred 1 where Rl ifi H, F, Cl, Br, CH3, OCH3, OCF2H, CF3, CH20CH3 or CH2SCH3, R i~ H or Cl-C2 alkyl, and Q i6 Q-l or Q-2;
3) Compounds of Preferred 2 where A i~ A-l. X is CH3, OCH3, Cl, Br or OCF2H. and Y i~ CH3, OCH3, cH2ocH3, NHCH3, C2H5~ CH(OCH3)2' cyclopropyl~
C-CH or C-CCH3;
4) Com2ound6 of Preferred 3 where Q i~ Q-l and Rl i6 H:

5) Compounds of Preferred 3 where Q i6 Q-2 and Rl i6 H;

6) Compound~ of Preferred 4 where ~ i~ 0;

7) Compound~ of PreferLed 4 where ~ i6 S:

8) Compound6 of ~referred 4 where ~ i~ NR3:

9) Compound6 of Preferred 5 where ~ i~ 0;

10) Compound6 of Preferred 5 ~here W i6 S;

11) Compounds of Preferred 5 where W i6 NR3;

12) Compound6 of Preferred 1 where A i~ A-l, Rl is ~ 3. CH3~ 0CF2H, CF3, CH20CH3 or CH2SCH3. R i6 H or Cl-C2 alkyl, ~ is CH3.
OCH3, Cl, Br or OCF2H, Y i5 CH3, OCH3. CH20CH3, NHC~3. C2H5. CH(OCH3)2. cyclop~opyl. C-CH or C-CCH3, and Q i~ Q-3 or Q-4;

13) Compound~ of Preferred 12 where ~ i6 Q-3 and Rl i6 H;

7~

14) Compound6 of Preferred 12 where Q i~ Q-4 and Rl is H:

15) Compound6 of Preferred 13 where ~ i6 0;
lS) Compound6 of Preferred 13 where W i6 S
17) Compound6 of PLeferred 13 where ~ i6 NR3;
la) Compound~ of Preferred 14 where ~ is 0;
19) Compound~ of Preferred 14 where ~ i6 S:
20) Compounds of Preferred 14 where W i6 NR3.
Compound~ of ~he invention specifically pre-ferred for reasons of higher herbicidal efficacy and/or greater ea~e of ~ynthe6i6 are:
o N-~(~,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methylbenzothiazole-4-6ulfonamide, m.p. 187-194C:
and ~ N-[(4-~etho~y-6-methyltriazin-2-yl)aminocarbonyl]-2-methylbenzothiazole-4-6ulfonamide, m.p. 182.5-183C.
Another embodiment of t~e present invention include~ compound~ of Formula I ~s defined above except whe~ein ~1 i6 0:
R7 i6 H:
R i6 H or Cl-C5 alkyl;
Rl i H, F, Cl, Br, CH3, OCH3 or OCF2H:

Z5 N ~ N ( 1 A i6 ~ O Z , N

A-l A-2 N
or ~ O ~ ;

i6 CH3, OCH3, OCH2CH3, Cl, F, Br, I, OCF2H, CH2F, OCH2CH~F, OCH2CH~2, OCH2CF3 or CF3; and Y i6 H, CH3, OCEI3, OC2H5, CH20CH3, 3 N(OCH3)CH3, N(CH3)2, CH2CH~, CF3, SCH3, OCH2CH=CH2, OCH2C-CH, CHzOCH2CH3, OCH2CH20CH3, CH25CH3, ~ R~. g L R ~ L
/ l--FH3 C~ J , OCP2H, S~P~H or cyclopropyl:

provided ~hat when X is Cl. F, Br or I, then Z i6 CH
and Y i8 OCH3, OC2H5, N(OCH3)CH3, NHCH3, N(CH3)2 o~
OCF2H; and their agriculturally ~uitable 6alt6.
The compounds of thi~ embodiment that are preferred for rea~on~ of greater herbicidal efficacy and/or increa~ed ease of synthe6i6 a~2:
1) Compound~ of Formula I where Q i~ Q-l and ~ i~ O or S;
2) Compounds of Preferred 1 where ~ is A-l, R
i~ H or CH3 and Rl i~ H, Cl, CH~ or OCH3;
3) Compound6 of Preferred 2 where Y i~ CH3.
3 2 H3. NHCH3, CH2CH3. CH(OCH3)2 or cyclo-propyl:
4) Compound~ of Preferred ~ where ~ is CH3, OCH3, Cl, B~ o~ OCF2H.
- The compounds of the inven~ion that are mo~t preferred for rea60n~ of higher herbicidal efficacy and/or greater ea~e of synthe6i6 are N-[(4.6-dimethoxy-pyrimidin-2-yl)ami~ocarbonyl]-2-methyl-4-benzothiazole-sulfonamide: and N-[(4-methoxy-6-methyl-triazin-2-yl)-aminocarbonyl]-2-methyl-4-benzothiazole~ulfonamide.

7~7 Detailed De6criptisn_of the Inve_tion sYnthe 6 i ~
~ he compound6 o~ Formula I can be prepared by one or ~re of the procedure6 ~hown belo~ in Eguation~
1, 2, and 3.
Equation 1 depict6 the reaction of sulfonyl isocyanate~ of Formula II with the appropriate heterocyclic amine6 III to give the de6ired product6 of Formula I.
Eauation 1 o C~502NCO ~ H2NA ~ QS02NHCNHA
II III I
wherein Q and A are as previou61y defined.

The reaction of Equation 1 i6 best carried out in an inert aprotic solvent, e.g. methylene chlor-ide, tetrahydrofuran, or acetonitrile at a temperat~rebetween 20~ and 80C. A cata~ytic amount of l,~-diaza-bicyclo[2.2.Z]octane (DABC0) may be u6ed to accelerate the reaction. In ca~e6 in which the produ~ts are in601ubl2 in the reaction ~olvent, they may be i60-lated by ~imple filtration. When the product6 are ~oluble, they may be i601ated by evaporatisn of the 601vent and trituration of the re~idue with ~olvent6 e.g. l-chlorobutane, diethyl ether, or methanol, and filtration.
Compound6 of Formula I oan al~o be prepared a6 ~hown in Equation 2 by ~reating 6ulfonamide6 o~
Formula IV with the methyl e~er of a pyri~idine or triazine carbamic a~id of Formula V in the pre6ence of an equimolar quantity of trimethylaluminu~.

" (CH ) Al QS02NH2 + CH30 IV V
wherein Q and A are a~ previou61y defined.

The reaction of Equation 2 i6 be6t carried out at temperature~ between 25 and ~3~C in a solYent, e.g.
methylene chloride or 1,2-dichloroethane for 12 to 96 hour~ under an inert atmo6phere. After being allowed to cool to room tempera~ure, the reaction lS mix~ure i6 acidified and the de6ired products are isolated by either filtration or e~traction with a solvent, e.g. methylene chloride or ethyl acetate.
The methyl carbamate~, V, can be convenien~ly 6ynthe-sized by trea~men~ of the corre6ponding heterocyclic amine~ of Formula III with dimethyl carbonate or methyl chloroformate in the pre6ence of a ba6e, e.g. s~dium hydride or pyridine.
Alternatively, compound6 of Formula I may be 6ynthe6ized a6 6hown in Equation 3 by the reaction of sulfonamide~ of Formula IV with the phenyl e6ter of an appropria~e carbamic a~id, VI.
Equation 3 o IV ~ PhOC~HA 1~ DBU >
2) H 0~ ~
VI
wherein Q and A are a~ previou~ly defined.

~2 ~7 The reaction s~own in Equation 3 i~ best carried out at Z5C in a solvent, e.g. dioxane or acetoni-trile in the presence of an equimolar quantity of a tertiary a~ine ba~e ~uch a6 l,5-diazabicyclot5.4.0~-undec-5-ene (DBU). After being stirred at ~oom temperature for one to three hour6, the reaction mixture i6 acidified and the de~i~ed produ~t i601ated eit~er by filtration or extraction with a 601vent, e.g ethyl acetate or methylene chloride. The phenyl carbamate6, VI, can be zynehesized by treating tbe corre6ponding ~eterocyclic amine~ of Formula III with diphenyl carbonate or phenyl chloroformate in the presence of a base, e.g. sodium hydride, pyridine, or potas6ium carbonate in eetrahydrofuran 601ution.
Sulfonyl i~ocyanate~ of Formula II ean be prepared a6 ~hown in Equation 4 by the reaction of 6ulfonamide6 of general structure IV with pho~gene in the pre6ence of n-butyl iRocyanate and a catalytic amount of l,4-diazabicyclo[2.2.2]octane (DABC0).
Equation_4 QS2NH2 COC12 3~QS02Nco IV xylene~ II
~ABC0 wherein Q i~ a~ previou~ly defined.

The reaction shown in Equation 4 i~ be6t carried out according to the method taught in United States Patent ~,23B,621.
The requi~ite 6ulfonamide~ of Formula IV can be 6ynthe6ized ~rom the corre6ponding ~ulfonyl chloride~
of Formula VII a6 outlined below in Equation 5.

~2~7~

E~uation_5 QS02Cl ~ QS2NH2 VII THF IV
wherein Q i~ as previou61y defined.

The reac~ion 6hown in Equation 5 i~ mo6t conveniently cacried ou~ by adding either exces6 anhydrou~ ammonia or concent~ated ammonium hydroxide to a solution of the ~ulfonyl chloride, VII, in a 6uitable 601vent, e.g. tetrahydrofuran or diethyl ether at -30C to 0C. The de6ired ~ulfonamide of Formula IV is i~olated by removal of the ~olvent in vacuo and either cry6tallization from a 601vent, e.g.
1-chlorobutane o~ ethyl acetate, or extraction with methylene chloride or ethyl acetate; re6idual ammonium chloride can be removed by wa6hinq with wa~er.
Sulfonyl chloride6 of Formula VII can be pre-pared by one or more of ~he method~ shown below in Equatisn6 6, 7, 8, or 9.
Equation 6 depi~ts the oxidative chlorination of ~lkyl thioether~ of Formula VIII, where W i~ 0 or NR3, to give 6ulfonrl chloride6 VIIa.
Equation 6 QSR8 H20 ~ Q502Cl VIII VIIa wherein R~ i~ C2-C~ alkyl or benzyl, Q i8 Q-l, Q-2, Q-3, or Q-4, and W i6 0 or NR3.

:~Z~7~7 The reaction shown in Equation 6 i~ be6t effected in a ~uitable solvent e.g. chlorofor~ or ~ethylene chloride; in 60me ca6e6, it i8 ad~antageou6 to u6e acetic acid a~ 601~ent. The reaction i~ car-5 ried out in ~he presence of at lea6t 2.5 equi~alent~of water and three equivalent6 of chlorine gas at tem-peratuee6 betwee~ 0 and 30C for one to five hour6.
The products are mo~t conveniently i601ated by removal of the ~olvent in vacuo and are normally carried on to the next ~tep without purification.
Another method for the preparation of 6ulfonyl chloride6, VIIb, i6 outlined in Equation 7 and involve6 the reaction of unsubstituted compounds of Formula IX
wi~h chloro6ul~0nic acid.
Equation 7 Q-H ClSO3H QSO2Cl I~ YIIb wherein Q is Q-l, Q-2, Q-3, Ol Q-4, and W is S or NR3.

The reaction of Equation 7 i6 be6t carried out by addition of the compound6 I~ eo excess chloro~ulfonic acid. The reaction mixture i6 then typically heated to 100-150C for one to f ive houræ. cooled to 25~C, and cautiou~ly poured onto cru~hed ice. The de6ired ~ulfonyl chloride6. VIIb, are i~olated by extraction wi~h a ~uita~le ~olvent , e.g.- ether, methylene chloride, or benzene, and can be carried on ~o the next 6tep wi~hou~ purification. In ca6e~ where the ~ulfonyl chlorides VIlb are obtained a~ cry talline ~olid~, it is often po6~ible to remoYe impuritie~ and unde6ired i60mer6 by recry6~allization from a 601vent 35 ~uch as petroleum e~her or hexane.

1~

A t~ird procedure for the 6ynthe6is o~ sulfonyl chloride6 of Formula VIIc involve6 the diazoti~aeion of aniline derivati~e6, ~, and coupling ~ith sulfur dioxide in t~e pre6ence of cupric chloride a6-æhown in 5 Eg,uat ion ~ .
on Q-NH2 1) NaN02. HCl QS02Cl 2) S02, CuC12 ~ VIIc wherein Q i6 Q~ -2, Q-3, or Q-4. and ~ is S or NR3.

The rea~tion ~hown in Equation 8 i6 accompli~hed by treating a 601ution of the aniline ~ in concentrated hydrochloric a~id wit~ an aqueou~ ~olution of 60dium nitri~e a~ -5 to 5C. After being s~irred for 10-30 ~inutes at absut 0C to ensure complete diazotization.
the ~olutîon i~ added to a mixture of exce~6 6ulfur dioxide and a catalytic amount of cuprou6 or cupric chloride in glacial acetic acid at about 10C. The temperature i6 ~aintained at about 10C for 0.25-1 hour, and i6 allowed to ri~e to 25~C where 6tirring is 25 continued for 2 to 24 hour6. Thi~ 601utio~ i6 then poured into a large exce6s o~ ice-water. The ~ulfonyl chloride6 VIIc ca~ be i601ated by ~iltration or by extraction with a ~olvent e g diethyl ether, methylene chloride, or l-chlorobutane.
Alternatively, 6ulfonyl chloride6 of Formula VIId can be prepared as 6hown below in Equation 9 by treatment of aryl bromidex, ~I, with a~ organometallic reagent ~ollowed by reaction with sulfuryl chloride.

279~
Equation 9 Q-Br1) Mg or QS02~1 n-BuLi 5 ~I2) S2C12 VIId wherein Q i6 Q-l or Q-2, R i~ C2-C5 alkyl, and Rl i5 ~, F, Cl. CH3, or OC~3.
The reaction of Equation 9 i6 mo~t conveniently carried out according to the procedure of S. N. Bhatta-charya, et al., J. Chem. Soc. ~C?, 1265 (196B). Thu6, a ~olution of ~he aryl bromide, ~I, in a 601vent,e.g.
diethyl ether or tetrahydrofuran is cooled to -78~C
under a~ inert atmosphere and treated with a slight exce~6 of an organome~allic reagent, e-y- n-butyl-lithium or phenyllithium (magne6ium can al60 be employed to ~enerate the Grignard reagent). The mixture i~ stirred at temperature~ be~ween -78 and ODC for 30 minute6 to one hour and i8 then quenc~ed with exce6~ sulfucyl chloride. Af~er being 6tirred at roo~ temperature for one to three hour6, the reaction mixture is poured onto ice and the de6ired 6ulfonyl chloEide~, VIId, are i601ated by extraction with a suitable 601vent e.g. methylene chloride or diethyl ether. Al~ernatively, the reaction mixture can simply be concentrated in vacuo ~o give the product6 VIId in a state 6uf f i~iently pure to be carried directly on to the next 6tep.
The requi~ite aniline derivatives of Formula ~
can be prepared in a 6traightforward manner by reduc- -tion of the cor~e6ponding nitro compound6 of Formula XII a6 ~hown in Equa~ion 10.

16 ~2~7~

quation 10 Q-N02 [Hl_~ Q-NH2 ~II X
wherein Q i~ Q-l, Q-2, Q-3, or Q-4, and W i6 S or NR3.

There exi~t~ a wide variety of methods for effecting the reduction of aromatic nitro derivatives tv the corre6ponding anilines. One of the more common procedure6 involve~ treating the nitro compound6 of Formula ~II with a ~light exce~ of 6tannou6 chloride dihydrate in concentrated hydrochloric acid or ethanol solution at temperature6 between 25 and 80C. Alter-natively, reduction can be accompli6hed with iron powder in glacial acetic acid 601ution a6 de6cribed by Hazlet and Dornfeld, J. Am. Chem. Soc., 66, 1781 (1944~. For a general review, 6ee Groggin6, "Unit Proce66es in Organic Synthe6i6", ~cG~aw-Hill Book Co., New York, 1947, pp. 73-128.
Many of the requisite intermediate6 mentioned above are either known in the literature or can be synthe6ized by method6 known ~o one who i~ skilled in the ar~. For example, alkyl thioether6 of Formula VIIIa, where Q i6 Q-l, can be prepared a6 6hown in Equation ll(a) by the reaction of an appropriately 6ub6tituted aniline of Formula ~IIIa with a carboxylic acid or it6 derivatiYe~. Similarly, compound6 of 30 FoYmulas I~a, ~Ia, and ~IIa can be synthe6ized by the reactions shown below in Equation6 ll(b), ll(c), and ll(d), respectively.

~L2~27~

Equation 11 (a) H

5Rl~NH2 RCOCl, r > R~ R
SR9 SR~
~IIIa VIIIa 10 (b) H H

~NH P~COC 1, or >Rl~N~R
2 (RCO~20 IVa I Xa ~c) ~ RCOCl, or ~Ia ( d ) }I H

Rl~NH2 E~CO 1, or ~ Rl~ R

gVIa 2~IIa wherein R, Rl and W are a6 previou61y def ined, and REI i~
C2-C4 alkyl or benzyl.

7gL7 This type of procedure can al~o be applied to ~he 6ynthe6i of alkyl thioet~ers of Formula VIIIb, where Q i~ Q-2, and to the preparation of compound6 of Formula6 IXb, ~Ib. and XIIb a6 6hown in Equation 12 5 (a-d).
Equation 12 (a) E~ ~

10Rl~N~2 I~C~ R~Nw\~R

SR8 S~B
~IIIb VlIIb (b) B

H2 C;, ~; ~D Rl~N~R

~ ' ~

(~
~ H

~1 ~ 2 RCOCl, or ~ 1 ~ N~R
~r ~RC0)2o ~r ~Vb ~Ib ~;22~7 (d) ~2 1 ~ 0~ r ~ ~H ~C~
~0 2 ~VIb ~IIb wherein R, R1 and W are a~ previou61y defined, and R8 i6 C2-C4 alkyl or benzyl.

The reaction6 outlined above in quations ll(a-d) and 12(a-d) ha~e recei~ed a qreat deal of 6tudy and are well precedented in the literature.
~enzothiazole~ (Q = Q-l or Q-2, and W = S) can be peepared according to the procedure of Hofmann, Ber., 12, 2359 (1~79): 13, 8, 1223 (lB80); 20, 1798 (1887).
For an excellent compilation of reference6 dealing with the 6ynthe6i6 of benzothiazoles, 6ee J. M.
Sprague and A. H. Land in "Heterocyclic Compound6", Vol. 5, ed. R. C. Elderfield, John Wiley and Son~, Inc., New York, 1957, pp. 506-518. Benzoxazole~ (Q =
Q-l or Q-2, and W = 0) can be prepared in an analogou6 fashion by treatment of the appropriate o-aminophenol6 with a carboxylic acid or it6 derivative~. For a general overview of the method6 known for the ~ynthe-6iS of benzoxazole~, ~ee J. W. Cornforth in "Hetero-cyclic Compound6", Vol. 5, ed. R. C. Elderfield, ~iley, New York, 1957, pp. 420-434. Finally, benz-imidazole~ (Q = Q-l or Q-2, and W = NR3) can be prepared by 6imilar me~hods as described by E. S.
Schipper and A. R. Day in ~'Heterocyclic Compounds", Vol. 5, ed. R. C. Elderfield, Wiley, New York, 1957, PP. 274-284.

12~7~

An alternate ~ynthe6i6 of benzothiazole6 of Formula6 VIIIa, IXa, ~Ia, XIla, and VIIlb, I~b, ~Ib and ~IIb, where ~ i S, involve6 an oxidatiYe cyclization of thioamide6 XVIIa and XVIIb a~ 6hown below in Equation 13(a,b).
Equation 13 (a) H

R~ 5 3 6 > R~

XVTIa VIIIa (Gl=SRB) I~a (Gl~H) ~Ia (Gl-Br) ~VIa (G7~N02) (b) H ~ H

~1~ K3Fe ( CN ) 6 P~--~[N\~R

~1 Cl 25~VIIb VIIIb (Gl=SR~) IXb (Gl=H) ~Ib (Gl=B~
VIb (Gl=NO

30 wherein R and Rl are a~ previou61y defined, and R~ i~
C2-C4 alkyl or benzyl.

~,~;22~

The reaction of ~quation 13 i6 be6t effected according to the procedure of Jacobson, ~er., 19, 1067, lall (1886); 20, 1895 (1887); 2Z, 904 (1~89~;
26, 2363 (1893). This reaction often afford6 mixtures S of regioi60meric benzothiazole6 ~hich can be 6éparated by chromatsgraphy or recry~tallization.
Many of the requi~ite indazole6 of For~ula~
VIIIc, IXc, and ~IIc, where Q i~ Q-3 or Q-4 and ~ is NR3, are either known in the literaeure or can be synthesized by me~hod6 known to one who i~ 6kill~d in ~he art. Equation 14(a) ~hows one of the more common procedure6 which involve~ cycliza~ion of the appro-priate bydrazone~, XVIIIa, i~ the pre~ence of a 6uitable base e.g. sodium hydroxide or potassium carbonate to give the desired products VIIIc, I~c, and ~IIc. Tbi6 ~ame type of reac~ion can be applied to the synthesis of indazole6 of Formulas VIlld, I~d, and ~IId, 6tartin~ from the corre~ponding bydrazones, ~VIIIb, as shown in Equation 14(~).
Equation 1-4 (a) C=NN~3 R ~

XVllIa VllIc (G2 SR8) IXc ( 2 Xllc (G2=N0 2~7 (b) ~ C-NN~3 R ~N

C2 ~2 Cz ~VIIIb VIIld (G =SR ) 2 a I~d (G2=H) ~IId (G2=N02) wherein Rl, R2, and R3 are a~ previou61y defined, Rg i6 N02, Cl, or Br and R8 i6 C2-C4 alkyl or benzyl.

~ hen Rg iz N02, She ~eaction~ of Equation~ 14 (a and b) can be mo~t conveniently carried out accord-ing to the procedure of Reich and Gaigailian, Ber., 46, 2380 ~1913); Meyer, Ber., 22, 318 (1889): and Dittrich and Meyer, Ann., 264, 131 (1891). When Rg i~ Cl or Br, the reaction6 of Equation 14 (a and b) are be6t performed according to the procedure of Fries and Tampke, Ann, 454, 270 (1927). For al~ernate syn-the6e6 of indazole~ such as VIII(c,d), IX(c,d), and ~II(c,d), refer eo Elderfield in "Heterocyclic Co~-pound~", Vol. 5, ed. R. C. Elderfield, Wiley, New York, 1957, pp. 163-182.
1,2-Benzi60xazole~ of Formula6 VIlIe and VlIIf, where Q i6 Q-3 or Q-~, and ~ i6 O, can be prepared by any one of a number of well-known method6. Equation 15(a,b) outline6 the reac~ion of ortho-6ub~tituted benzoyl compound~, e.g. ~a and ~b, with hydroxyl-amine to ~ive t~e corre6ponding oxime6, ~IXa and ~I~b, which are directly t~eated with alkali to afford the de6ired product~, VIIle and VIIIf, re~pectively.

~az~z7~

Eaua~ton 15 (a) ~a IXa VIIIe (b) _ _ 15 1~ ~ ~
R~S ~2 R8S ~2 R~S a2 XXb ~IXb VIIIf wherein Rl and R2 are a6 previously defined, R8 is C2-C4 alkyl or benzyl, and Rlo i6 Br, Cl, I, F, or N02.

The reaction of Equation 15 is best accomplished by the procedure of Cathcart and Meyer, Ber. Deut.
Chem. Ges., 25, 1498(1~92j. A modification of this general type of re~action can also be appli2d to the 6ynthesis of 1,2-benzisoxazole6; 6ee Lindemann and Thiele, Ann. Chem., 449, 63 (1926). Fo~ a review of alternative synthese6, refer to K . -H. Wunsch and A. J.
Boulton, AdY. Heterocyclic Chem., 8, 277 (1967).
1,2-Benziso~hiazoles of Formulas IXe, ~IIe, IXf, and ~IIf, where Q is Q-3 or Q-4, and n i6 S, can also be prepared by one or more of several pos~ible proce-dures; one such method is shown below in Equation 3L2~2~
2516(a,b). Thu6, ami~ot~iol6 of ~ormula~ ~la or ~Ib are treated wlth an oxidizing agent, e.g. iodine, bromine, or pota~6ium ferricyanide to give t~e de6ired products IXe, ~IIe, I~ or ~IIf.
EQuation 16 (a, R~ 2 ~ r~

~XIa I~e (G3=H) IIe (G3=N2 (b~ ~
H H

Rl ~ o~ G3 Z
~b I~f (G3=H) ~IIf (G3SN0 wherei~
Rl and R2 are as previou61y defined.

The reaction of Equation 16 i6 most ea6ily carried out according to the procedure o Goerdeler and Randler, Chem. Ber., 92, 1679 (1959). Alternate ~ynthe6e~ of 1,2-benzi60thiazoles have been reviewed by ~. Davi6 in Adv. Heteroc~clic Chem., 14, 43 (1972).
The 6ynthe6i~ of heterocy~lic amine8 ~ e. g.
tho6e repcesented by Formula III ha6 been reviewed in "The Chemi6try of Heterocy~lic Compounds", a ~erie6 publi6hed by In~er6cience Publ., New York and London.

~2~Z~

Aminopyrimidines are described by D.J. Brown in "The Pyrimidines", Vol XVI of the series mentioned above.
The 2-amino-1,3,5-triazines of Formula III, where A is A-l and Z is N, can be prepared according to methods described by E.M. Smolin and L. Rapaport in "s Triazines and Derivatives", Vol. XIII.
Pyrimidines of Formula III, where A is A-l and Y
is an acetal or thioacetal substituent, can be prepared by methods taught in European Patent Application No. 84,224 (published July 27, 1983.) Pyrimidines of Formula III, where A is A-l and Y
is cyclopropyl or OCF2H, can be synthesized according to the methods taught in South African Patent Application No. 837,434 and South African Publication No. 82/5045, respectively, Compounds of Formula III, where A is A-2 or A-3, can be prepared by procedures disclosed in United States Patent 4,339,267.
Compounds of Formula III, where A is A-4, can be prepared by methods taught in European Patent Application No. 45,677 (published March 3, 1982).
Compounds of Formula III, where A is A-5, can be prepared according to the methods taught in U.S. Patent 4,421,550.
Compounds of Formula III, where A is A-6 and A-7, can be synthesized by procedures taught in U.S. Patent 4,496,392 and in European Publication No. 125,864 (published November 21, 1984).
Additional references dealing with the synthesis of bicyclic pyrimidines of Formula III, where A is A-2, A-3, or A-4 are Braker, Sheehan, Spitzmiller and Lott, J. Am, Chem.
Soc., 69 3072(1947); Mitler and Bhat~acharya, Quart. J. Indian Chem. Soc., 4, 152 (1927); Shrage and Hitchings, J. Org. Chem., . _ _ 16, 1153 (1951); Caldwell, Kornfeld and Donnell, J. Am. Chem.

~2~279~7 Soc., 63, 218~ (1941); and Fissekis, Myles and Brown, J. Org. Chem., 29, 2670 (1964).

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by treating compounds of Formula I with a solution of an alkali or alkaline earth metal salt haviny a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydride).
Quaternary amine salts can be made by similar tech-niques. Detailed examples of such techniques are given in United States Patent 4,127,405.

The compounds of this invention and their preparation are further illustrated by the following examples.

Example 1 2-Methyl-4-benzothiazolesulfonyl chloride 2-Methylbenzothiazole (50 g) was added in a slow, dropwise manner to 86 mL of chlorosulfonic acid at room temperature. When the addition was complete, the dark reaction mixture was heated at 140-145C for about 3 hours. The solution was allowed to cool and was slowly added to a large excess of ice. Insoluble solids were removed by filtration and the aqueous layer was extracted with benzene. Drying and evapor-ation of the solvent gave an off-white solid which was shown by lH NMR analysis to consist of a mixture of sulfonyl chlorides, presumably the 4-, 6-, and 7-iso-mers. This crude material was recrystallized three times from hexane to remove the 6-isomer as a white solid~ m.p. 100-102C. The combined mother liquors ~Z;~7~

were concentrated to give a dark yellow oil which was carried on to the next step without further purifi-cation.
Example 2 2-Methyl-4-benzothiazolesulfonamide A solution of 18 g of the product from Example 1 in 170 mL of tetrahydrofuran was cooled to O~C under an atmosphere of nitrogen and treated with 5 mL of anhydrous ammonia. The mixture was stir~ed at room temperatuLe for about an hour, filtered to remove the ammonium chloride, and the filtrate concentrated in vacuo to give an off-white solid. Thi6 crude product was purified by silica gel chromatography: elution with ethyl acetate-hexanes (3:1) gave 1.9 g of 2-methyl-4-benzothiazolesulfonamide as a white powder, m.p. 236-Z39C; NMR (DMS0-d6/CDC13): ~ 2.95 (3H, 5), 7-0 (2H, br s, S02NH2), 7.55 (lH, t, J=~Hz), B.0 (lH, dd, J=2,8Hz), 8.2 (lH, dd, J=2,8Hz).
ExamPle 3 N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methy~-4-benzothiazolesulfonamide A solution of 0.23 g of the p~oduct from Example 2 and 0.28 g of 4,6-dimethoxypyrimidin-2-ylcarbamic acid, phenyl ester in 5 mL of dry acetonitrile was treated at room tempe~ature with 0.15 mL of i,5-diaza-bicyclo[S.4.0]undec-5-ene (DBU), added over a period of about one minute. The reaction solution was stir-~ed at room temperature for 1.5 hour and was then diluted with 2 mL of wa~er and acidified by the ad~ition of 5% aqueous hydrochloric acid. The resulting p~ecipitate was collected by filtration, washed well with wate~ and ether, and dried. The yield of N-[(4,~-dimethoxypyrimidin-2-yl)amino-carbonyl]-2-methyl-4-benzothiazole~ulfonamide was 0.21 g as a white powder, m.p. 187-194~C.

2~

af~27 NMR (CDC13/DMS0-d5): ~ 2.7 (3H, s), 4.05 (6H, 8), 5.8 (lH, s), 7.5 (lH, t, J=8Hz), 8.15 (lH, dd, J=2,8Hz), 8.25 ~lH, dd, J=2,~Hz), 8.7 (lH, br ~), 13 3 (lH, br 8); IR(KBr): 3330, 1730, 1610, 13$0, 1160 cm Example 4 3-Nitroacetanilide A 6uspension of 13.8 g of 3-nitroaniline and 20 mL of triethylamine in 200 mL methylene chloride was cooled to 0C under a nitrogen atmosphere and treated with 10.~ g of acetyl chloride, added in a dropwi6e manner. The reaction mixture was allowed to warm to room temperature overnight. Removal of the volatiles in vacuo gave a crude yellow 601id which was washed with 5% aqueou6 hydrochloric acid, water and wa6 then dried. The yield of 3-nitroacetanilide wa6

17.4 g a~ a light yellow 601id, m.p. 147-149C;
NMR (CDC13/DMS0-d6): ~ 2.1 (3H, br 6), 7.5 (lH,t, J=9Hz), 8.0 (2H,br t), B.6 tlH,br 6) 10.1 (lH, br s);
IR(KBr): 1675, 1550, 1525, 1350 cm ExamPle 5 3-Nitrothioacetanilide A mixture of 5 g of the product from Example 4 and 4.7 g of 2,4-bi6(4-methoxyphenyl)-1,3-dithia-2,4-dipho6phetane-2,4-di6ulfide ("Lawe660n' Reagent") in 30 mL of dry ~oluene wa6 heated at 100C under an atmosphere of nitrogen for a period of 4 hour6. The solvent was removed in vacuo, the residue was taken up in diethyl ether, washed with several portions of 30 water, dried and concentrated to give an orange solid. Thi6 crude material was purified by passage through a column of silica gel. Elution with ether-hexane (1:1) afforded 5.6 9 of 3-nitrothioacetanilide as a yellow 601id, m.p. 90-93C; NMR (CDC13/DMS0-d6):
~ 2.7 (3H, 6), 7.6 (lH, t, J=8Hz), 8.05 tlH, dd, J=2,8Hz), B.3 (lH, dd, J=2,8Hz), 9.05 (lH, br s), 11.8 (lH, br 6 ) .
2g ~Z~274,~

Example 6 2-Methyl-7-nitrobenzothiazole To a 6tirred suspen~ion of 28.2 g of pota6sium ferricyanide in 39 mL water at room temperature wa~
S added, ~imultaneou61y, 41 mL o~ 8% aqueou6 60dium hydroxide and 6 g of the product from Example 5.
AfteL completion of the addition, the reaction mixture was stirred at room temperature for 1.5 hour6. The insoluble olids were 6eparated by filtration, washed with wa~er, and then dis601ved in 40 mL of 20~ aqueous hydrochloric acid. After being heated on the steam bath for 15 minutes, this aqueou6 solution wa6 fil-tered hot. The filtrate was allowed to cool and was diluted with three times it~ volume of cold water.
The re~ulting 601id6 were filtered and recrystallized from ab601ute ethanol to give 2.9 g of an off-white ~olid, m.p. 102-105C. Analy~i6 by lH NMR showed thi6 material to be a mixture of the 7- and 5-nitro isomer6. A second recry6tallization from ethanol gave a ~a~nple of pure 2-methyl-7-nitrobenzothiazole as a white ~olid, m.p. 120-121C; NMR(CDC13): ~ 2.9 t3H, ~), 7.7 (lH, t, J=8Hz~, B.4 (2H, br t).
Exam~le 7 2--Methyl-7-aminobenzothiazole To a 601ution of 3.8 g of the product from Example 6 and 8.1 g of glacial acetic acid in 56 mL
absolute ethanol at reflux temperature wa6 added 3.8 g of iron powder in small portion6. The reaction mix-ture wa~ heated at reflux temperature for about 36 houL~, and wa~ then cooled and filtered. The ~iltrate wa~ concentrated in vacuo and the residue treated with several mL cold water to give a solid. Filtration and drying gave 2.2 g of the title compound as a tan-colored 601id, m.p. 100-101C; NMR (CDC13): ~ 2.8 (3H, 6), 3.9 (2H, br s), 6.65 ~lH, d, J=8Hz), 7.2 (lH, t, J=8Hz), 7.5 (lH, d, J=8Hz).

7~7 3~
Example 8 2-MethYl-7-benzothiazole6ulfonamide A ~uspen6ion of 8 g of the product from Example 7 in 20 mL of concentrated hydrochloric acid wa~
cooled ~o 0C and treated wi~h a solution of 3.7 g sodium nit~ite in 6 mL of wa~er. After completion of the addition, the mixture was stirred at 0-5~C for about 15 minute6. This diazonium salt 601ution was then added all at once to a mixture of liquid sulfur dioxide, 2 g of cupric chloride dihydrate, and ~ mL
water in 39 mL of glacial acetic acid at about lO~C:
vigorous gas evolution ensued. Thi6 reaction mixture was 6tirred at room temperature for another 4 hours, and wa6 then poured into 190 mL ice-water. The resulting precipitate wa6 collected by filtration, wa~hed with water, and dried to give 9.2 g of 2-methyl-7-chloro6ulfonylbenzothiazole as a yellow powder, m.p. 93-97C, dec; IR(KB~): 1380, 1175, 800, 770, 720 cm~l.
Example 9 2-MethYl-7-benzothiazolesulfonamide A ~olution of 9.2 g of the product from Example B in 74 mL of dry tetrahydrofuran wa6 cooled to O~C
under nitrogen and treated with 2.5 mL of anhydrous ammonia. After being 6tirred at room temperature for 2 hour6, the mixture wa6 filtered and the solid6 collected were washed well with water and methylene chloride. The yield of 2-methylbenzothiazole-7-6ulfonamide wa~ 5.1 ~ as a white solid, m.p.
223-224~C. NMR (DMS0-d /CDC13): ~ 2.9 (3H, s) 7.1-7.9 (2H, br s), 7.7 (lH, t, J=9Hz), 8.1 (lH, br d), 8.2 (lH, br d); IR(K~r): 3300, 3000, 1350, 1160, 1150 cm~l.

~ d~fD~
..~7~'7 Example 10 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methyl-7-benzo~hiazole~ulfonamide A ~u6pension of 1.5 g of the product from Exam-ple 9 in 33 mL of 1,2-dichloroethane wa6 cooled to 0C
under a nitrogen atmosphere and treated with 3.6 mL of trimethylaluminum (2M 601ution in toluene). The mix-ture was warmed briefly to 50-60DC, recooled to room temperature, and ~reated with 1.4 g of 4-me~hoxy-6-methylpyrimidin-2-yl-carbamic acid, methyl e6ter.
Thi6 reaction mixture wa6 heated at reflux temperature f or approximately 48 hour6 and wa~ then cooled to 0C
and acidified by the addition of 5% aqueou6 hydro-chloric acid. The re6ulting precipitate wa6 separated by fi}tration and wa6hed with water and l-chlorobutane.
The filtrate wa6 dried over magnesium 6ulfate, treated with carbon, and concentrated in vacuo to give a yellow gum. Cry6tallization from hot acetonitrile afforded 0.45 g of the title compound a6 an off-white 601id, m.p. 178-180C: NMR (CDC13): ~ 2.5 (3H, 6), 2.8 (3H, 6), 3.9 (3H, 6), 6.3 (lH, 63, 7.5-7.8 (lH, br 6), 7.6 (lH, t), 8.2 (2H, br d); IR(KBr): 1710 (car-bonyl 6tretch) cm 1.

Utilizing the procedure6 of Equation~ 1-16 and Example~ 1-10, the following compound6 may be prepared by one 6killed in the art.

~22274~7 Table 1 N
QSO2NHCNH~
O N

Q W R 1 2 3 ~ Y m.P.(oc) 10 Q-l S H H - - CH3 OCH3 Q-l S CH3 5-F - - CH3 OCH3 Q-l 5 CH3 6-Cl - - CH3 OC~3 Q-l S CH3 5-Br - - CH3 OCH3 Q-l S CH3 6-CH3 - - CH3 OCH3 15 Q-l S CH3 5 O 3 3 OCH3 Q-l S CH3 6-OCFzH - - CH3 OCH3 Q-l S C2H5 H - - CH3 OC~3 Q-l S i_C3H7 H - - CH3 OCH3 Q-l S t-C4Hg H - - CH3 OCH3 20 Q 1 S CH3 H - - CH3 CH3 190-193(d) Q-l S CH3 H - - CH3 OCH3 190-191 Q-l S CH3 H - - OCH3 OCH3 187-194 Q-l S CH3 H - - OCH2CH3 CH3 Q-l S CH3 H - - Cl OCH3 25 Q-l S CH3 H - - F OCH3 Q-l S CH3 H - - Br OCH3 Q-l S CH3 H - - I OCH3 Q-l S CH3 H - - OCF2H CH3 Q-l S CH3 H - - CH2F CH3 30 Q-l S CH3 H 2 2 3 Q-l S CH3 H 2 2 3 Q-l S CH3 H - - OCH2CF3 CH3 Q-l S CH3 H - - CF3 CH3 Q-l S CH3 H - - CH3 H

35 Q-l S CH3 H - - CH3 CH2OCH3 ~Z227~

Table l (continued) Q W E~ Rl R2 R3 ~ y m.P~-(oc) Q-l S CH3 H 3 HCH3 Q-l S CH3 H - - CH3 N(OCH3)CH3 Q-l S CH3 H - - CH3 N(CH3~2 Q-l S CH3 H - - CH3 CH2CH3 Q-l S CH3 H 3 CH3 Q-l S CH3 H - - CH3 OCH2CH=CHz 1 Q-l S CH3 H - - CH3 OCH2C-CH
Q-l S CH3 H 3 CE~20CH2CH3 Q-l S CH3 H 3 CH2CH20CH3 Q-l S CH3 H - - CH3 CH~SCH3 Q-l S CH3 H ~ - CH3 CHO
15 Q-l S CH3 H CH3 COCH3 Q-l S CH3 H - - CH3 CH(OCE~3)2 Q-l S CH3 H - - CH3 CH(OCH3)SCH3 Q-l S CH3 H - - CH3 CH(OCH2CH3)SCH3 Q-l S CH3 H - - CH3 CH(OCH2CH3)0CH3 Q-l S CH3 H _ _ CH3 C(oCH3)2CH3 Q-l S CH3 H ~ - CH3 C(OCH3)(SCH3)CH3 O~
Q-l S CH3 H CH3 ~ O J
O~
Q-l S CH3 H - - CH

Q-l S CH3 H
O~
Q-l S CH3 H 3 CH

Q-l S CH3 H - - CH3 S

C~3 S

~L2~

able 1 (continued) R Rl R2 ~3 ~ Y m P.(CL
O~,CH3 5 Q-l S CH3 H _ _ CH3 ~ J
O ~,~H3 Q-l S CH3 H ~ ~ CH3 ~ S J

10 Q-l S CH3 3 CH~ S
Q-l S CH3 H ~ ~ CH3 SCF2H
Q-l S CH3 H _ _ CH3 ~
Q-l O H H _ _ OCH3 OCH3 Q-l O CH3 5-F _ _ OCH3 OCH3 Q-l O CH3 6-Cl - - 3 3 Q-l O CH3 5-Br - - 3 3 Q-l O CH3 6-CH3 _ _ OCH3 OC~3 Q-l O CH3 5-OCH3 _ _ OCH3 OCH3 20 Q-l O CH3 6-OCF2~ - - 3 3 Q-l O C2H5 H _ _ OCH3 0 3 Q-l O l-C3H7 H - - 3 3 Q-l O t-C4Hg H - - 3 3 Q-l N H H - CH3 OCH3 OCH3 25 Q-l N CH3 5-F - H OCH3 OCH3 Q-l N CH3 6-Cl - H OCH3 3 Q-l N CH3 5-Br - H OCH3 OCH3 Q-l N CH3 6-CH3 - H OCH3 3 Q-l N CH3 5-OCH3 - H OCH3 OCH3 30 Q-l N CH3 6-OCF2H - H 3 3 Q-l N C2H5 H - H OC 3 3 Q-l N i-C3H7 H - H OCH3 OC 3 Q-l N t-C4~9 ~ - H OCH3 3 Q-2 S H H ~ ~ CH3 OCH3 35 Q-2 S CH3 H ~ ~ CH3 CH3 ~L~2~

Table 1 (continu~dl Q W R 1 2 3 ~ Y ~ P.(C) Q-2 S CH3 H ~ ~ CH3 OCH3 178-180 5 Q-2 S CH3 H _ _ OCH3 OC~3 175-1 a o Q-2 S CH3 5-F ~ ~ CH3 OC~3 Q-2 S CH3 6-Cl ~ ~ CH3 OCH3 Q-2 S CH3 5-Br ~ ~ CH3 OCH3 Q-2 S CH3 6-CH3 ~ ~ CH3 ~CH3 10 Q-2 S CH3 5-OCH3 ~ ~ CH3 OCH3 Q-2 S CH3 6-OCF2H ~ ~ CH3 OCH3 Q-2 S C2H5 H ~ ~ CH3 OCH3 Q-2 S i_C3H7 H ~ ~ CH3 OCH3 Q-2 S t-C~Hg H ~ ~ CH3 OCH3 15 Q-2 O H H ~ ~ CH3 ~CH3 Q-2 0 CH3 H ~ ~ CH3 OCH3 Q-2 0 CH3 5-F ~ ~ CH3 OCH3 Q-2 O CH3 6-Cl ~ ~ CH3 OCH3 Q-2 0 CH3 5-B~ ~ ~ CH3 OCH3 20 Q-2 O CH3 6-CH3 ~ ~ ~H3 OCH3 Q-2 O CH3 5-OCH3 ~ ~ CH3 OCH3 Q-2 O CH3 6-OCF2H ~ ~ CH3 OCH3 Q-2 O C2H5 H ~ ~ CH3 OCH3 Q-2 O i_C3H7 H ~ ~ CH3 ~CH3 25 Q-2 O t-C4Hg H ~ ~ ~H3 CH3 Q-2 O t-C4Hg H ~ ~ CH3 OCH3 171-175 Q-2 O t-C4Hg H _ _ OCH3 OCH3 Q-2 M CH3 5-F - H CH3 ~CH3 30 Q-2 N CH3 6-Cl - H CH3 OC~3 Q-2 N CH3 5-Br - H CH3 OCH3 Q-2 N CH3 5-OCH3 ~ H CH3 OCH3 Table 1 ~continued~

R Rl R2 ~3 ~ Y m.P.( Q-2 N i-C3H7 H _ H CH3 OCH3 Q-2 N t-C4Hg H _ H CH3 OCH3 Q-3 S - H El - CH3 OCH3 Q-3 S - 6-Cl H - CH3 OCH3 10 Q_3 S - 5-Br H - CH3 OCH3 Q-3 S _ 5-OCH3 H - CH3 OCH3 Q-~ S - 6-OCF2H H - CH3 OCH3 15 Q_3 O _ H CH3 - CH3 OCH3 Q_3 9 - 6-Cl H - CH3 OCH3 Q-3 O - 5-Br H - CH3 OCH3 Q-3 o - 6-CH3 H - CH3 OCH3 20 Q_3 O - 5-OCH3 H - CH3 OCH3 Q-3 N _ H H CH3 CH3 OCH3 ~-3 N - H C~3 CH3 OCH3 Q-3 N _ 5-F H H CH3 OCH3 25 Q_3 N - 6-Cl H H CH3 OCH3 Q-3 N - 5 B~ H H CH3 OCH3 Q-3 N _ 6-OCF2H H H CH3 OCH3 30 Q_4 S - H H - CH3 OCH3 Q-4 S - 6-Cl H - CH3 OCH3 Q-4 S - 5-Br H - CH3 OCH3 35 Q_4 S - 6-CH3 H - CH3 OCH3 ~ o 9~7 Tabl2 1 ~continued) Q W R ~ 2 R3 X Y m P.(C) Q~4 S _ 5-OCH H - CH3 OCH3 Q_4 S - 6-OCF2H H - CH3 OCH3 Q-4 O - 6-Cl H - CH3 OCH3 Q-b O - 5-Br H - CH3 OCH3 Q-4 ~ - H H CH3 CH3 OCH3 15 Q-4 ~ - H CH3 H CH3 OCH3 Q-4 ~ - 5-F H H CH3 OCH3 Q-4 ~ - 6-Cl H H CH3 OCH3 Q-4 ~ - 5-Br H H CH3 O~H3 Q 4 ~ 3 3 3 Q-4 ~ - 5-OCH3 H H CH3 OCH3 Q-l S CH3 H - _ CH3 CH(OCH2CH3)2 Q-l S CH3 H _ _ CH3 CH(OCH3)SCH2CH3 Q-l S CH3 H - _ CH3 CH(OCH2CH3)SCH2CH3 25 Q-l S CH3 H _ _ CH3 CH(SCH3)2 Q-l S CH3 H - _ CH3 CH(SCH2CH3)2 Q-l S CH3 H _ _ CH3 CH(SCH2CH3)SCH3 Q-l S CH3 H _ _ CH3 C(CH2CH3)2CH3 Q-l S CH3 H - - CH3 CtOCH3)(0CH2CH3)CH3 Q-l S CH3 H - - CH3 C(OCH3)(SCH2CH3)CH3 Q-l S CH3 H _ _ CH3 C(OCH2CH3~(SCH3)CH3 Q-l S CH3 H 3 2 3 2 3 3 Q-l S CH3 H _ _ CH3 C(SCH3)2CH3 7~7 Table 1 tcontinued) Q ~ R Rl R2 ~3 ~ y m p.
Q-l S CH3 H - - CH3 C~SCH2CH3~2CH3 Q-l S CH3 H - - CH3 C(SCH2CH3)(SCH3)CH3 Q-l S CH3 H CH3 O

~ Q-l S CH3 H _ _ CH3 Q-l S CH3 H _ _ CH3 C ~ S~

~5 O
Q-l S CH3 H _ CH3 Q-l S CH3 H _ _ CH3 O

Q-l S CH3 H _ _ CH3 Q-l S CH3 H _ _ C~3 ~ ~

O CH
Q-1 S CH3 H _ _ CH3 C ~ 0 Q-l S CH3 H _ _ CH3 CHX S

Q 1 5 C 3 3 ~ S

~o Table 1 tcontinu~d) m.p.
Q W R Rl 2 3 ~ Y (~C) 5 Q-l S CH3 H ~ ~ CH3 C-CH
Q-l S CH3 H ~ ~ CH3 C-CCH3 Q-l S CH3 H ~ - OCH3 CH20CH3 Q-l S CH3 H ~ ~ OCH3 NHCH3 Q-1 S CH3 H ~ ~ OCH3 CH2CH~
10 Q-l S CH3 H ~ ~ OCH3 CH(OCH3)2 Q-l S CH3 H _ _ OCH3 ~
Q-l S CH3 H ~ ~ OC~3 C-CH
Q-l S CH3 H ~ ~ OCH3 C-CCH3 15 Q-l S CH3 H - - C1 NHCH3 Q-l S CH3 H _ _ Br NHCH3 Q-l S CH3 H _ _ OCF2H OCH3 Q-l S CH3 H - _ OCF2H CH20CH3 Q-l S CH3 H _ _ OCF2H NHCH3 Q-l S CH3 H - - OCF2H CH2CH3 Q-l S CH3 H _ _ OCF2H CH(OCH3)2 O-l S CH3 H - - OCF2 ~
Q-l S CH3 H _ _ OCF2H C-CH
Q-l S CH3 H _ _ OCF H C-CCH

Q-l S CH 6-CH20CH3 ~ ~ CH3 OCH3 Q-l S CH 5-CH2SCH3 ~ ~ CH3 OCH3 Q-l S H 5-F ~ ~ CH3 OCH3 Q-l S H 6-Cl ~ ~ CH3 OCH3 30 Q-l S H S-Br ~ ~ CH3 OCH3 Q-l S H 6-CH3 ~ ~ CH3 OCH3 Q-l S H 5-OCH3 ~ ~ CH3 OCH3 ~22~

T~bl ~
m.p.
R Rl ~2 R3 X Y (C) Q-l S H 6-OCF2H~ CH3 OCH3 5 Q-l S H 5-CF3~ ~ CH3 OCH3 Q-l S H 6-CH2OCH3 ~ ~ CH3 OCH3 Q-l S H 5-CH2SCH3 ~ ~ CH3 OCH3 Q-l S CH2CH3 5-F~ ~ CH3 OCH3 Q-l S CH2CH3 6-Cl~ ~ CH3 OCH3 10 Q-l S CH~CH3 5-Br~ ~ CH3 OCH3 Q-l S CH2OE13 6-CH3CH3 OCH3 Q-l S CH2CE13 S-OCH3CH3 OC~3 Q-l S CH2CH3 6-OCF2H~ ~ CH3 OCH3 Q-l S CH2CH3 5-CF3CH3 OCH3 Q-l 5 CH2CH3 5-CH2SCH3 ~ ~ CH3 OCH3 Q-l O H 5-F _ _ OCH3 3 Q-l O H 6-Cl _ _ OCH3 O 3 Q-l o ~ 5-Br _ _ OCH3 OCH3 20 Q-l O H 6-CH3_ _ OCH3 OCH3 Q--l O H 5-OCH3_ _ OCH3 O 3 Q-l O H 6-OCF2H_ _ OCH3 OCH3 Q-l O H 5-CF3- - OCH3 3 Q-l O H 6-CH2OCH3 - - OCH3 3 25 Q-l O H 5-CH2SCH3 - - 3 3 Q-1 O CH3 H _ _ OCH3 O 3 Q-l O CH3 5-CF3 - - OCH3 3 Q-l O CH3 6-CH2OCH3 - ~ 3 3 Q-l O CH3 5-CH2SCH3 - - OCH3 3 Q-l O CH2CH3 6-Cl - - OCH3 3 Q-l O CH2CH3 5-Br_ _ OCH3 O 3 Q-l O CH2CH3 6-CH3- - OCH3 OC~3 Q 1 O C~2CH3 3OCH3 3 35 Q-l O CH2CH3 6-OCF2H_ _ OCH3 ~CH3 ~4~7 Table 1 tcontinuedL
m.p.
Q W R Rl R2 R3 X Y
Q-l O CH2CH3 5-CF3 - -OCH3 OCH3 Q-l O CH2CH3 5-CH~OCH3 - - 3 3 Q-l O C~2CH3 6-CH2SCH3 - - ~ 3 3 Q-l N H H _ HOCH3 OCH3 Q-l N H 5-F _ H 3 3 Q-l N H 6 Cl _ H 3 3 10 ~-1 M H 5-Br _ ~OCH3 O 3 Q-l N H 6-CH3 _ HOCH3 OC 3 Q-l N H 5-OCH3 _ HOCH3 OCH3 Q-l N H 6-OCF2H - HOCH3 O 3 Q-l N H 5-CF3 - HOCH3 3 15 Q-l N H 6-CH2OCH3 - H OCH3 C 3 Q-l N H 5 C 2 3 HOCH3 OCH3 Q-l N H 6-F _ CH3 OCH3 OCH3 Q-l N H 5-Cl - CH3 OCH3 OCH3 Q-l N H 6-B~ - CH~ OCH3 OCH3 - Q-l N H 6-OCH3 - CH3 OCH3 OCH3 Q-l N H S-OCF2H - CH3 OCH3 OCH3 Q-l N H 6-C~3 - CH3 OCH3 OCH3 Q-l N H 5-CH2OCH3 - CH3 OCH3 OCH3 25 Q-l N H 6-CH2SCH3 - CH3 OCH3 OCH3 Q-l N CH3 H _ H OCH3 O 3 Q-l N CH3 5-CF3 - H OCH3 3 Q-l N CH3 6 CH2 3 H OCH3 3 ~-1 N CH3 5 CH2S 3 H OCH3 3 3o Q-l N CH3 H _ CH3 OCH3 OCH3 Q-l N CH3 5-F _ CH3 OCH3 OCH3 Q-l N CH3 6-Cl - CH3 OCH3 OCH3 Q_l N CH3 5-Br - CH3 OCH3 OCH3 Q-l N CH3 6-CH3 - CH3 OCH3 ~3 Q-l N CH3 5-OCH3 - CH3 OCH3 OCH3 ~L2~

Table 1 ~ontinued) Q ~ R Rl R2 R3 ~ y (C) Q-l N CH3 6-OCF2H - CH3 OCH3 OC 3 5 Q-l N CH3 5-CF3 - CH3 OCH3 OCH3 Q-l N CH3 6-CH2OCH3- CE~3 OCH3 OCH3 Q-l N CH3 5 2 3 CH3 OCH3 OCH3 Q-l N C~2CH3 5-F - H OC 3 3 Q-l N CH2CH3 6-Cl - H OCH3 3 10 Q-l N CH2CH3 5-Br ~ H OCH3 3 Q-l N CH2CH3 6-CH3 H OCH3 3 Q-l N CH2CH3 5-OCH3 - H OCH3 3 Q-l N CH2CH3 6-OCF2H - H OCH3 3 Q-l N CH2CH3 5-CF3 H OCH3 3 15 Q-l N CH2CH3 6-CH2OCH3 ~ H OCH3 3 Q-l N CH2CH3 5-CH25CH3 - H OCH3 3 Q-l N CH2CH3 H - CH3 OCH3 OCH3 Q-l N C~2CH3 5-F - CH3 OCH3 OCH3 Q-l N CH2CH3 6-Cl - CH3 OCH3 OCH3 Q-l NCH2CH3 6 CH3 CH3 OCH3 OCH3 Q-l NCH2CH3 5-OC~3 CH3 OCH3 OCH3 Q-l NCH2CH3 6-OCF2H ~ CH3 OCH3 OCH3 Q-l NCH2CH3 5-CF3 CH3 OCH3 OCH3 25 Q-l NCH2CH3 6-CH2OCH3 - CH3 OCH3 OCH3 Q-l NCH2CH3 5-CH25CH3 CH3 OCH3 OCH3 Q-2 S CH3 5-CF3 ~ ~ CH3 OCH3 Q-2 S CH3 6-CH2OCH3 ~ ~ CH3 OCH3 Q-2 S CH3 5-CH2SCH3 ~ ~ CH3 OCH3 30 Q-2 S H 5-F ~ ~ CH3 OCH3 Q-2 S H 6-Cl ~ ~ CH3 OCH3 Q-2 S H 5-B~ ~ ~ CH3 OCH3 Q-2 S H 6-CH3 ~ ~ CH3 OC~3 Q-2 S H 5-OCH3 ~ ~ CH3 OC~3 35 Q-2 S H 6-OCF2H ~ ~ ~H3 OCH3 ~;Z2~791~

Table 1 (continued) Q ~ R 1 2 3 ~ Y SC) Q-2 S H 5-CF3 ~ ~CH3 OCH3 Q-2 S H 6-CH2OCH3 ~ ~CH3 OCH3 Q-2 S H 5-CH2SCH3 ~CH3 OCH3 Q-2 S CH2CH3 5-F ~ ~CH3 OCH3 Q-2 S CH2CH3 6~Cl ~ ~CH3 OCH3 Q-2 S CH~CH3 5-~ ~ ~CH3 OCH3 10 Q-2 S CH2CH3 ~-CH3 ~ ~CH3 OCH3 Q-2 S CH2CH3 5-CF3 CH3 OC~13 Q-2 S CH2CH3 6-CH2OCH3 ~ ~CH3 OCH3 Q-2 O CH3 5-CF3 ~ ~CH3 OCH3 Q-2 0 CH3 6-CH2OCH3 ~ ~CH3 OCH3 Q-2 O CH3 5-CH2SCH3 ~ ~C~3 OCH3 Q-2 N H H _ HCH3 OCH3 20 Q-Z N CH3 H _ HCH3 OCH3 Q-2 N CH3 5-CF3 - HCH3 oc~3 Q-2 N CH3 5-F _ CH33 OCH3 25 Q-2 N CH3 6-Cl -CH33 OCH3 Q-2 ~ CH3 5-B~ - 33 OCH3 Q-2 N CH3 5-OCH3 -CH3 3 ~CH3 Q-2 N CH3 6-OCF2H _CH3CH3 OCH3 30 Q-2 N CH3 5-CF3 _CH3C 3 OCH3 Q_3 ~ _ 5-CF3 H ~CH3 OCH3 35 Q-3 S - 6-CH2OCH3 H ~CH3 OCH3 ~2~7~

Table 1 (continu~d) Q W R Rl R2 R3 ~ y m.P.~C2 Q-3 5 - 6-Cl CH3 - CH3 OCH3 Q-3 S - 5-Hr CH3 - CH3 OCH3 10 Q_3 S - 6-OCF2H CH3 - CH3 OCH3 Q-3 S - s-CF3 CH3 - CH3 OCH3 Q-3 0 - 6-CF3 H _ CH3 OCH3 Q-3 N - 6-CH2OCH3 HH C~13 OC~3 Q~3 N - H ~ H CH3 OCH3 Q-4 S - s-CF3 H _ CH3 OCH3 ~5 Q-4 S - 6-Cl CH3 - CH3 OCH3 Q-4 S - 5-Br CH3 - CH3 OCH3 30 Q_4 S - 5-CF CH3- CH3 OCH3 Q_4 o - 5-CF3 H_ CH3 OCH3 ~L2~:~27~7 Table_l (continued) W R Rl ~2 ~3 ~ Y m.P.L~-c) ~L~2~7417 Table 2 N~
QSO2NHCNH_~ O N
O N--~

- Q ~ R R1 R2 R3 ~ Y m D (~C~

Q-1 S CH3 6-C1 ~H3 ~C~3 Q-1 S CH3 5-Br CH3 OCH3 Q-1 S t-C4H9 H CH3 OCH3 25 Q-l S CH3 OCH2CH2F CH3 Q-l S CH3 H OCH~CHF2 CH3 Q-1 S CH~ H CF3 CH3 Q- 1 S CH3 H CH3 N(OCH3)CH3 Q- 1 5 CH3 H CH3 N(CH3)2 .

'~2;~

Table 2 (continued~

Q W R Rl R2 R3 ~ y .m.P.(~C) Q-l S CH3 H - - CH3 OCH2CH=CH2 Q-l S CH3 H - - CH3 OCH2C-CH
Q-l S CH3 H 3 2 2 3 Q-l S CH3 H - - CH3 OCH2CH20CH3 Q-l S CH3 H - - CH3 CH2SCH3 10 Q-l S CH3 H ~ - CH3 CHO
Q-l S CH3 H ~ - CH3 ~OCH3 Q-l S CH3 H - - CH3 CH(OCH3)2 Q-l S CH3 H - - CH3 CH(OCH3)SCH3 Q-l S CH3 H - - CH3 CH(OCH2CH3)SCH3 15 Q-l S ~H3 H - - CH3 ~H(OCH2CH3)0CH3 Q-l S CH3 H _ _ C~3 C(OCH3)2CH3 Q-l S CH3 H ~ - CH3 C(OCH3)(5CH3)CH3 o Q-l S CH3 H - - CH
2~ O
Q-l S CH3 H CH3 ~ S~

Q-l S CH3 H C~3 Q-l S CH3 H CHX O

Q-l S CH3 H - - CH

Q-l S CH3 H - - CH

.~L~7~7 Table 2 (continued) W R Rl ~2 ~3 ~ Y ~ P~
O`~,C~3 5 Q-l S CH3 H _ _ CH3 ~ J

Q_l S CH3 3 10 Q-l S CH3 H ~ ~ CH3 SCF2H
Q-l S CH3 H _ _ CH3 ~
Q-l O H H _ _ OC~3 OCH3 Q-l O CH3 5-F _ _ OCH3 3 Q-l O CH3 6-Cl - - OCH3 3 Q-l O CH3 5-Br _ _ OCH3 O 3 Q-l O CH3 6-CH3 _ _ OC~3 OCH3 O-l O CH3 5-OCH3 _ _ OCH3 O 3 Q-l O CH3 6-OCF2H - - OCH3 3 Q-l O C2H5 H _ _ OCH3 3 Q-l O i-C3H7 H _ _ OCH3 OCH3 Q-l O t-C4H9 H - - OCH3 3 Q-l N H H - CH3 OCH3 OCH3 Q-l ~ CH3 5-F - H OCH3 3 Q-l N CH3 6-Cl - H OCH3 3 Q-l N CH3 5-Br - H OCH3 3 Q-l N CH3 6-CH3 - H 3 3 Q-l N CH3 5-OCH3 - H OCH3 3 Q-l N CH3 6-OCF2H ~ H OCH3 3 Q-l N C2H5 H - H OCH3 3 30 Q-l N i_C3H7 H - H OCH3 3 Q-~ N t-C4Hg H _ H 3 3 Q-2 S H H ~ ~ CH3 OCH3 Q-2 S CH3 H ~ ~ CH3 CH3 Q-2 S CH3 H ~ ~ CH3 OC~3 35Q-2 S CH3 H _ _ OCH3 OCH3 152-156(d) 4g ~1.22Z~

Table 2 (continuedl Q ~ R 1 2 3 ~ Y m.~.(C) Q-2 S CH3 5-F ~ ~ CH3 OCH3 5 Q-2 S CH3 6-Cl ~ ~ CH3 OCH3 Q-2 S CH3 5-Br ~ ~ CH3 OCH3 Q-2 5 CH3 6-CH3 ~ ~ CH3 OCH3 Q-2 S CH3 5-OCH3 ~ ~ CH3 OCH3 Q-2 S CH3 6-OCF2H ~ ~ CH3 OCH3 10 Q-2 S C2H5 H ~ ~ CH3 OCH3 Q-2 S i_C3H7 H ~ ~ CH3 OCH3 Q-2 S t-C4H9 H ~ ~ CH3 OCH3 Q-2 O H H ~ ~ CH3 OCH3 Q-2 O CH3 H ~ ~ CH3 OCH3 15 Q-2 O CH3 5-F ~ ~ CH3 OCH3 Q-2 O CH3 6-Cl ~ ~ CH3 ~CH3 Q-2 O CH3 5-B~ ~ ~ CH3 OCH3 Q-2 O CH3 6-CH3 ~ ~ CH3 OCH3 Q-2 O CH3 5-OCH3 ~ ~ CH3 OCH3 20 Q-2 O CH3 6-OCF2H ~ ~ CH3 OCH3 Q-2 O C2H5 H ~ ~ CH3 OCH3 Q-2 O i-C3H7 H ~ ~ CH3 OCH3 Q-2 O t-C4Hg H ~ ~ CH3 CH3 Q-2 O t-C4Hg H ~ ~ CH3 OCH3 149-153 ~5 Q-2 O t-C4H9 H _ _ OCH3 3 Q-2 N CH3 6-Cl - H CH3 OCH3 Q-2 N CH3 5-Br - H CH3 OCH3 Q-2 N C2H5 ~ - H CH3 OC~3 Q-2 N t-C4H9 H - H CH3 OCH3 ;27~7 Table 2 (continued~

Q W R 1 2 3 ~ Y m.p. (C) Q-3 S - 6-Cl H _ CH3 OCH3 Q-3 S - 5-B~ H - CH3 OCH3 Q-3 S - 6-CH3 H _ CH3 OCH3 10 Q_3 S - 5-OCH3 H _ CH3 OCH3 Q-3 O - H H _ CH3 OCH3 Q-3 O - 5-F H _ CH3 OCH3 Q_3 o - 6-Cl ~ - CH3 OCH3 Q-3 o - 5-Br H _ CH3 OCH3 Q-3 O - 6-CH3 H _ CH3 OCH3 Q-3 O - 5-OCH3 H _ CH3 OCH3 20 Q_3 N - H H CH3 CH3 OCH3 Q-3 ~ - 5-F H H CH3 OCH3 Q-3 N - 6-Cl H H CH3 OCH3 Q-3 N - 5-B~ H H CH3 OCH3 25 Q_3 N - 6-CH3 H H CH3 OCH3 30 Q_4 S ~ 5-F H _ CH3 OCH3 Q-4 S - 6-Cl H _ CH3 OCH3 Q-4 S - 5-B~ H _ CH3 OCH3 Q-~ S - 6-CH3 H _ CH3 OCH3 ~;~22'7~

Table 2 (continued) Q W R 1 2 3 ~ Y m p.

5 Q-b O - H CH3 - CH3 OCH3 Q-4 o - 6-C1 3 3 Q-4 O - 5-Br H - CH3 OCH3 Q-b ~ _ H H CH3 CH3 OCH3 Q-4 ~ - H CH3 H CH3 OCH3 Q-b ~ _ 5-F U H CH3 OCH3 Q_~ ~ _ 6-Cl H H 3 3 Q_4 ~ - 5-Br H H CH3 OCH3 Q_4 ~ - 6-CH3 H H CH3 OCH3 Q_4 ~ _ 5-OCH3 H 3 3 Q-4 ~ - 6-OCF2H H H CH3 OCH3 Q-l S CH3 H _ CH3 CH(OCH2CH3)2 Q-l S CH3 H _ _ CH3 CH(OCH3)SCH2CH3 Q-l S CH3 H 3 2 3 2 3 Q-l S CH3 H - - CH3 CH(SCH3)2 Q-l S CH3 H - CH3 CH(SCH2CH3)2 Q-l S CH3 H _ _ CH3 CH(SCH2CH3)SCH3 Q-l S CH3 H _ _ CH3 C(CH2CH3)2CH3 Q-l S CH3 H - - CH3 C(OCH3)(0CH2CH3)CH3 Q-l S CH3 H _ _ CH3 C(OCH3)(SCH2CH3)cH3 Q~l S CH3 H _ _ CH3 C(ocH2cH3~(scH3)cH3 Q-l S CH3 H 3 ( 2 3 2 3 3 Q-l S CH3 H - - CH3 C(SCH3)2CH3 Q-l S CH3 H _ _ CH3 C(SCH2CH3)2CH3 4-1 S CH3 H - CH3 C(scH2cH3)(scH3)cH3 Table 2 ( con~ i nued ~

Q li~ R Rl P~2 E~3 ~ y m.~ C) O
Q- 1 5 CH3 H _ _ CH3 >(~

Q- 1 S CH3 H _ _ CH3 S

Q- 1 S CH3 H - - CH3 ~ S~

Q-l S CH3 E~ CH3 S

Q- 1 S CH3 H _ _ CH3 o /
Q- 1 S CH3 H _ _ CH3 S o Q- 1 S CH3 H ~ CH3 X
2 5 C~3 S
Q-l S CH3 H _ _ ~<O~CH3 Q- 1 S CH3 H _ _ CH3 Q-1 S CH3 H _ _ CH3 Table ? (continued) m.p.
Q W R ~1 R2 ~3 ~ Y ~C~
5 Q-l S CH3 H ~ ~ CH3 C-CH
Q-l S CH3 H ~ ~ CH3 C-CCH3 Q-l S CH3 H _ _ OCH3 CH2OCH3 Q-l S CH3 H _ _ OCH3 NHCH3 Q-l 5 CH3 H _ _ OCH3 CH2CH3 10 Q-l S CH3 H _ _ OCH3 CH(OCH3)2 Q-l S CH3 H _ _ OCH3 ~
Q-l S CH3 H _ _ OCH3 C-CH
Q-l S CH3 H _ _ OCH C-CCH
Q-l S CH3 5-CF3 ~ ~ CH3 OCH3 Q-l S CH3 6-CH2OCH3 ~ ~ CH3 OC~3 Q-l S CH3 S-CH2SCH3 ~ ~ CH3 ~CH3 Q-l S H 5-F ~ ~ CH3 OCH3 Q-l S H 6-Cl ~ ~ CH3 OCH3 Q-l S H 5-Br ~ ~ CH3 OCH3 20 Q-l S H 6-CH3 ~ ~ CH3 OCH3 Q-l S H 5-OCH3 ~ ~ ~H3 OCH3 Q-l S H 6-OCFzH ~ ~ CH3 OCH3 Q-l S H 5-CF3 ~ ~ CH3 OCH3 Q-l S H 6-CH2OCH3 ~ ~ CH3 OCH3 Q-l S H 5-CH2SCH3 ~ ~ CH3 OCH3 Q-l S CH2CH3 5-F ~ ~ CH3 OCH3 Q-l S CH2CH3 6-Cl ~ ~ CH3 OCH3 Q-l S CH2CH3 5-~r ~ ~ CH3 OCH3 Q-l S CH2CH3 6-CH3 ~ ~ CH3 OCH3 Q-l S CH2CH3 5-OCH3~ ~ ~ CH3 OCH3 Q-l S CH2CH3 5-CF3 ~ ~ CH3 OCH3 Q-l S CH~CH3 6-CH2OCH3 ~ ~ CH3 OCH3 .1 252 7 ~ 7 Table 2 lcontinued) m.p.
Q W R RlR2 R3 :~ y ~C) Q-l O H 5-F~ ~ OCH3 OCH3-5 Q-l O H 6-Cl~ ~ OCH3 OCH3 Q-l O H 5-Br~ ~ OCH3 OCH3 Q-l O H 6-CH3~ ~ OC~3 OCH3 Q-l O H 5-OCH3~ ~ OCH3 OCH3 Q-l O H 6-OCF2H~ ~ OCH3 OCH3 10 Q-l O H 5-CF3~ ~ OCH3 OCH3 Q-l O H 6-CH2OCH3 ~ ~ OCH3 OCH3 Q-l O H 5-CH2SCH3 ~ ~ OCH3 O~H3 Q-l O CH3 H ~ ~ OCH3 OCH3 Q-l O CH3 5-CF3 ~ ~ OCH3 OCH3 15 Q-l O CH3 6-CH2OCH3 ~ ~ OCH3 OCH3 Q-l O CH3 5-CH2SCH3 ~ ~ OCH3 OCH3 Q-l O CH2CH3 5-F~ ~ OCH3 OCH3 Q-l O CH2CH3 6-Cl~ ~ OCH3 OCH3 Q-l O CH2CH3 5-B~~ ~ OCH3 OCH3 20 Q-l O CH2CH3 6-CH3OCH3 OCH3 Q-l O CH2CH3 5-OCH3OCH3 OCH3 Q-l O CH2CH3 6 2OCH3 OCH3 O-l O CH2CH3 5-CF3~ ~ OCH3 OCH3 Q-l O CH2CH3 5-CH2OCH3 ~ ~ OCH3 OCH3 Q-l N H H _ H OCH3 OCH3 Q-l N H 5-F _ H OCH3 OCH3 Q-l N H 6-Cl - H OCH3 OCH3 Q-l N H S-Br - H OCH3 OCH3 30 Q-l N H 6-CH3~ H OCH3 OC~3 Q-l N H 5-OCH3- H OCH3 OC~3 Q-l N H 6-OCF2H- H OCH3 OCH3 Q-l N H 5-CF3- H OCH3 OCH3 Q-l N H 6 C~2C 3H OCH3 OCH3 35 Q-l N H 5 CH2SC 3 H OCH3 ~CH3 ~22279~

Table 2 (continued) m.p.
Q ~ R R1 R2 R3 Q-1 N H 5-F_ CH3 OCH3 C 3.
5 Q-l N H 6-Cl- CH3 OCH3 OCH3 Q-l N H S-Br- CH3 OCH3 OCH3 Q-l N H 6-CH3- CH3 OCH3 OCH3 Q-l N H S-OCH3- CH3 OCH3 OCH3 Q-l N H 6-OCF2H- CH3 OCH3 OCH3 10 Q-l N H 5-CF3- CH3 OCH3 OCH3 Q-l N H 6 C 2 3CH3 OCH3 OCH3 Q-l N H 5 CH2 3CH3 OCH3 OCH3 Q-l N CH3 H_ H OCH3 3 Q-l N CH3 S-CF3- H OCH3 3 15 Q-l N CH3 6 CH2 3H 3 3 Q-l N CH3 5 CH2 3H OCH3 O 3 Q-l N CH3 H_ CH3 OCH3 OCH3 Q-l N CH3 5-F_ CH3 OCH3 OCH3 Q-l N CH3 6-Cl- CH3 OCH3 OCH3 20 Q-l N CH3 5-Br- CH3 OCH3 OCH3 Q-l N CH3 6-CH~- CH3 OCH3 OCH3 Q-l N CH3 5-OCH3 - CH3 OCH3 OCH3 Q-l N CH3 6-OCF2H - CH3 OCH3 OCH3 Q-l N CH3 5-CF3- CH3 OCH3 OCH3 25 Q-l N CH3 6 CH2 3 CH3 OCH3 OCH3 Q-l N CH3 5 CH2S 3 CH3 OCH3 OCH3 Q-l N CH2CH3 5-F - H OCH3 3 Q-l N CH2CH3 6-Cl - H OCH3 3 Q-l N CH2CH3 5-~3r - H OCH3 3 30 Q-l N CH2CH3 6-CH3 ~ H OCH3 3 Q-l N CH2CH3 5-OCH3 _ H 3 3 Q-l N CH2CH3 6-C~2H ~ H OCH3 3 Q-l N CH2CH3 5-CF3 H OCH3 3 Q-l N CH2CH3 6-C~2OCH3 H OCH3 3 35 Q-l N CH2CH3 2 3 ~CH3 OCH3 ~22;2~7~7 Table 2 (continued) Q W R Rl a2 R3 X Y (C) Q-l N ~H2CH3 H ~ CH3 OCH3 OCH3 5 Q-l N CH2CH3 5-F ~ CH3 OCH3 OCH3 Q-l N CH2CH3 6-Cl - CH3 OCH3 OCH3 Q-l N CH2CH3 5-Br - CH3 OCH3 OCH3 Q-l N CH2CH3 6-CH3 CH3 OCH3 OCH3 Q-l N CH2CH3 5-OCH3 CH3 OCH3 OCH3 10 Q~l N CH2CH3 6-OCF2H - CH3 OCH3 OCH3 Q-l N CH2CH3 5-CF3 CH3 OCH3 OCH3 Q-l N CH2C~3 6-CH2OCH3 ~ CH3 OCH3 OCH3 Q-l N C~2CH3 5-CH25CH3 ~ CH3 OCH3 OCH3 Q-2 S CH3 5-CF3 ~ ~ CH3 OCH3 15 Q-2 S CH3 6-CH2OCH3 ~ ~ CH3 OCH3 Q-2 S CH3 5-CH25CH3 ~ ~ CH3 OCH3 Q-2 S H 5-F ~ ~ CH3 OCH3 Q-2 S H 6-Cl ~ ~ CH3 OCH3 Q-2 S H 5-Br ~ ~ CH3 OCH3 20 Q-2 S H 6-CH3 ~ ~ CH3 OCH3 Q-2 S H S-OCH3 ~ ~ CH3 OCH3 Q-2 5 H 6-OCF2H ~ ~ CH3 OCH3 Q-2 S H 5-CF3 ~ ~ CH3 OCH3 Q-2 S H 6-CH2OCH3 ~ ~ CH3 OCH3 25 Q-2 S H 5-CH2SCH3 ~ ~ ,CH3 OCH3 Q-2 S CH2CH3 5-F ~ ~ CH3 OCH3 Q-2 S CH2CH3 6-Cl ~ ~ CH3 OCH3 Q-2 5 CH2CH3 5-B~ ~ ~ CH3 OCH3 Q-2 S CH2CH3 6-CH3 ~ ~ CH3 OCH3 30 Q~2 S CH2CH3 5-OCH3H ~ ~~ CH3 OCH3 Q-2 S CH2CH3 ~ CH3 OCH3 Q-2 S CH~CH3 5-CF3 ~ ~ CH3 OCH3 Q-2 S CH2CH3 6-C~2OCH3 CH3 OCH3 Q-2 S CH2CH3 5-C~25CH3 CH3 OCH3 35 Q-2 O CH3 5-CF3 ~ ~ CH3 OCH3 ~L~2Z7~7 Table 2 tcontinued) m.p.
Q ~ R Rl R2 R3 X Y . (~C) Q-2 N H H _ H CH3 OCH3 Q-2 N CH3 H _ H CH3 OCH3 Q-2 N CH3 5-CF3 _ H CH3 OCH3 Q-2 N CH3 6-F _ CH3 CH3 OCH3 Q-2 N CH3 5-Cl _ CH3 CH3 OCH3 Q-2 N CH3 6-Br _ CH3 CH3 OCH3 15 Q-2 N CH3 5-CH3 _ CH3 CH3 OCH3 Q-2 N CH3 6-OCH3 - CH3 CH3 OC~3 Q-2 N CH3 5-OCF2H _ CH3 CH3 OCH3 Q-2 N CH3 6-CF3 _ CH3 CH3 OCH3 Q-2 N CH3 5-CH2OCH3 _ CH3 CH3 OCH3 20 Q-2 N CH3 6-CH2SCH3 _ CH3 CH3 OCH3 Q-2 N CH2CH3 H _ CH3 CH3 OCH3 Q-3 S _ 5-CF3 H _ CH3 OCH3 Q-3 S _ 6-CH2OCH3 H - CH3 OCH3 Q-3 S _ 5-CH2SCH3 H - CH3 OCH3 25 Q-3 S _ 5-F CH3 - CH3 OCH3 Q-3 S _ 6-Cl CH3 - CH3 OCH3 Q-3 S _ 5-Br CH3 - CH3 OCH3 Q-3 S _ 6-CH3 CH3 - CH3 OCH3 30 Q-3 S _ 6-OCF2H CH3 - CH3 OCH3 Q-3 S _ 5-CF3 CH3 - CH3 OCH3 Q-3 o - 6-CF3 H _ CH3 OCH3 ,. :

~2~

Table 2 (continue~l W R Rl R2 R3 X Y m.D.~C) Q-3 N - 6-CH20CH3 H H CH3 OCH~

Q-4 S - 5-CF3 H _ CH3 OCH3 Q-4 S - 5-Br CH3 - CH3 OCH3 15 Q_4 S - 6-CH3 CH3 - CH3 OCH3 Q-4 S - 6-OCF~H CH3 - CH3 OCH3 Q-4 S - s-CF3 CH3 - CH3 OCH3 Q-4 S - 5-CH2SCH3 CH3 ~ CH3 OCH3 Q-4 O - 6-CF3 H _ CH3 OCH3 Q_4 N - 5-CF H H CH3 OCH3 3~

~2Z;~

Table 3 ~ 1 QS02NHCNH~
O N ~ ~

Q W R 1 2 3 1 1 m.v.(C) 10 Q-l S H H _ _ CH3 O
Q-l S CH3 5-F _ _ CH3 O
Q-l S CH3 6-Cl - - CH3 O
Q-l S CH3 S-Br _ _ CH3 O
Q-l S CH3 S-CH3 ~ ~ CH3 CH2 15 Q-l S CH3 5-OCH3 ~ ~ CH3 CH2 Q-l S CH3 6-OCF2H ~ ~ CH3 CH2 Q 2 5 ~ CH3 o Q-l S i C3H7 H CH3 0 Q-l S t-C4H9 H ~ ~ CH3 C~2 20 Q-l S CH3 ~ - - OCH3 0 Q-l S CH3 H _ _ CH2cH3 O
Q-l S CH3 H _ _ OCF2H O

Q-l 0 CH3 5-F _ _ OCH3 0 Q-l O CH3 6-Cl - - OC~3 O
Q-l O CH3 5-Br - - OCH3 Q-l O CH3 6-CH3 ~ ~ OCH3 CH2 Q-l O CH3 5-OCH3 ~ ~ OCH3 CH2 Q-l O CH3 6-OCF2H ~ ~ OCH3 C~2 30 Q-l O C2H5 H ~ ~ OC~3 CH2 Q-l O i-C3H7 H - - OCH3 O
Q-l O t-C H H _ _ OCH3 0 Q-l N H H CH3 C~3 O

35 Q-l N CH3 6-Cl - H CH3 0 7~

Table 3 Lcontinued2 Q ~ R Rl R2 R3 Xl Yl ~.P.(C) Q-l N CH3 5-Br - H CH3 O
Q-l N CH3 6-CH3 - H CH3 O
Q-l N CH3 5-OCH3 - H CH3 o Q-l N CH3 6-OCF2H - H C~3 O
Q-l N C2H5 H - H CH3 CH~
Q 1 N i C H H - H CH3 CH2 Q-l N t-C4H9 H ~ H CH3 CH2 Q-2 S H H ~ ~ CH3 CH2 Q-2 S CH3 5-F ~ ~ CH3 CH2 Q-2 S CH3 6-Cl ~ ~ CH3 CH2 Q-2 S CH3 5-Br ~ ~ CH3 CH2 Q 2 S CH3 6-CH3 ~ ~ CH3 CH2 Q-2 S CH3 5-OCH3 ~ ~ CH3 CH2 Q-2 S C2H5 H _ _ CH3 O
Q-2 S i_C3H7 H _ _ CH3 O
Q-2 S t-C4Hg H _ _ CH3 O

Q-2 O CH3 5-F _ _ CH3 O
Q-2 O CH3 6-Cl - - C~3 O
Q-2 O CH3 5-Br - - CH3 O

Q-2 O CH3 5-OCH - - C~3 O

Q-2 O C2H5 H ~ ~ CH3 CH2 Q 2 O i C H H ~ ~ CH3 CH2 Q-2 O t-C4H~ H ~ ~ CH3 CH2 Q-2 N CH3 5-F - H CH3 ~H2 Q-2 N CH3 6-Cl - H CH3 CH2 Q-2 N CH3 5-Br - H CH3 CH2 79~'7 Table 3 (continued~

Q W R ~1 R2 R3 ~1 Yl P.~C) Q-2 N CH3 6-OCF2H _ H CH3 CH2 Q-2 N C2H5 H _ H CH3 O
0-2 N l-C3H7 H _ H CH3 O
Q-2 N ~-C4~9 H - H CH3 O

10 Q_3 S _ H CH3 - CH3 O

Q-3 S - 6~Cl H - CH3 O
Q-3 S - 5-Br H - CH3 O
Q-3 S _ 6-CH3 H _ H3 CH2 Q-3 S _ S-OCH3 H _ CH3 CH2 Q-3 S _ 6-OCF2H H _ CH3 CH2 Q-3 O - H H _ CH3 CH2 Q-3 O - H CH3 _ CH3 CH2 Q-3 O - 5-F H _ CH3 CH2 20 Q_3 O _ 6-C1 H _ CH3 CH2 Q-3 O - 5-Br H - CH3 O
Q-3 o - 6-C~3 H _ CH3 O
Q-3 - 5-QCH3 H _ CH3 O

25 Q_3 N _ H H CH3 CH3 O
Q-3 N _ H CH3 HCH3 O

Q-3 N - 6-Cl H HCH3 O
Q-3 N - 5-Br H HCH3 O
30 0_3 N _ 6-CH3 H H 3 2 Q-3 N _ 5-OCH3 H H 3 H2 Q-3 N _ 6-OCF2H HCH3 CH2 Q-4 S _ H H - 3 2 Q-4 S _ H CH3 - 3 2 35 Q-4 S - 5-F H _CH3 CH2 :~2~ 7 Table 3 (continued) Q W R ~l ~2 R3 ~1 Yl m.P.~oc) Q-4 S _ 6-Cl H ~ CH3 CH2 5 Q-4 S - 5-Br H ~ CH3 CH~
Q-4 S _ 6-CH3 H _ CH3 0 Q-4 S _ 5-OCH3 H _ CH3 O
Q-4 S _ 6-OCF2H H _ CH3 0 l0 Q_4 o - H CH3 - CH3 O

Q-4 O - 6-Cl H - CH3 O
Q-4 O - 5-~r H ~ CH3 CH2 Q-4 O - 6-CH3 H ~ CH3 CH2 l5 Q_4 0 _ 5-OCH3 H ~ CH3 CH2 Q-4 O - 6-OCF2H H ~ CH3 CH2 Q-4 N _ H H CH3 CH3 CH2 Q-4 N _ H CH3 H CH3 CH2 Q- 4 N _ 5-F H H CH3 CH2 20 Q_4 N - 6-Cl H H CH3 O
Q-4 N - 5-Br H H CH3 0 Q-4 N _ 6-CH3 H H CH3 O
Q-4 N _ 5-OCH3 H H CH3 O
Q-4 N _ 6-OCF2H H H CH3 O
25 Q-l S CH3 5-CF3 CH3 CH2 Q-l S CH 6-CH2OCH3 ~ ~ CH3 CH2 Q-l S CH3 5-CH2SCH3 ~ ~ ~H3 CH2 Q-l O CH3 5-CF3 _ _ OCH3 CH2 Q-l O CH3 6-CH2OCH3 - - OCH3 C 2 Q-l O CH3 5-CH2SCH3 _ _ OCH3 CH2 Q l N CH3 3 H CH3 O
Q-l N CH3 6-CH~OCH3 - H CH3 Q

Q-l N CH3 s-Cff25CH3 - H CH3 O
Q-l S H 5-F - - CH3 O
35 Q-l S H 6-Cl - - CH3 O

~2~

Table 3 tcontinued?

Q W R Rl , R2 R3 ~1 Yl m.~.(C) Q-l S H 5-Br - - CH3 0 5 Q-l S H 6-CH3 - - CH3 0 Q-l S H 5-OCH3 - - CH3 0 Q-l S H 6-OCF2H - - CH3 0 Q-l S H 5-CF3 - - CH3 0 Q-l S H 6-CH20CH3 - - CH3 0 10 ~-1 S H 5 CH2SCH3 - - CH3 0 Q-2 S CH3 H_ ~ ~ CH3 2 Q 2 S CH3 5 3 CE~3 CH2 Q-2 S CH3 6-CH2~CH3 ~ ~ CH3 2 Q-2 S CH 5-CH2SCH3 _ _ CH3 C 2 15 Q~2 0 CH3 H - - CH3 0 Q-2 N CH3 H _ H 3 2 20 Q-2 N CH3 s-CF3 H CH3 CH2 Q-3 S _ 5-CF3H ~ ~H3 2 Q-3 S _ 6-CH20CH3 H ~ CH3 2 25 Q_3 S - 2 33 2 Q 3 s - 5-CF3H - CH3 0 Q-3 S _ 6-CH20CH3 H - CH3 0 Q-3 S _ 5-CH2SCH3 H - CH3 0 Q-3 N - H H H CH~ CH2 Q_3 N - S-CF3 H H CH3 C 2 Q-3 N _ 6-CH20CH3 H H CH3 2 Q-3 N _ 5-CH2SCH3 H H CH3 2 35 Q_4 S - 5-CH2SCH3 H - CH3 0 27~

Table 3 (con~inued~

5~ W R P~ l R 2 P~ 3 ~ 1 Y ~
Q_~, o - s-CF3 H _ CH3 CH2 Q-4 0 - 6-CH20CH3 H ~ CH3 2 Q_4 o - 5-CH2SCH3 H ~ CH3 2 Q- 4 N _ 5 - CF 3 H H CH3 0 Q-4 N _ 6-CH20CH3 H H CH3 0 Q-4 N _ 5-CH2SCE~3 H H CH3 0 2~

~;~22~

Table 4 QS02NHCNH~ O ~
O N ~ o J

~ W R Rl R2 R3 Xl m.P.(~C) 10 Q_l S H H ~ ~ CH3 Q-l S CH3 5-F ~ ~ CH3 Q-l S CH3 6-Cl ~ ~ CH3 Q-l S ~H3 S-Br ~ ~ CH3 Q-l S CH3 6-CH3 ~ ~ CH3 15 Q-l S CH3 5-OCH3 ~ ~ CH3 Q-l S CH3 6-OCF2H ~ ~ CH3 Q-l S C2H5 H ~ ~ CH3 Q-l S l-C3H7 H ~ ~ CH3 Q-l S t-C4Hg H ~ ~ CH3 20 Q-l S CH3 H ~ ~ OCH3 Q-l S CH3 H _ _ OCH2 3 Q-l S CH3 H _ _ OCF2H
Q-l O H H - - OCH3 Q-l CH3 5-F ~ ~ OCH3 25 Q l CH3 6-Cl ~ ~ OCH3 Q-l CH3 5-B~ ~ ~ OCH3 Q-l CH3 6-CH3 ~ ~ OCH3 Q-l CH3 5-OCH3 ~ ~ OCH3 Q-l CH3 6-OCF2H ~ ~ OCH3 30 Q~l C2H5 H ~ ~ OCH3 Q-l O l-C3H7 H ~ ~ OCH3 Q-l O t-C~Hg H - - OCH3 Q-l N H H ~ CH3 CH3 Q-l N CH3 5-F _ H CH3 35 Q-l W CH3 6-Cl ~ ~ CH3 Table 4 tcontinued~

W R R1 R2 R3 Xl m.~.(C~
Q-l N CH3 5-Br - H CH3 Q-l N CH3 6-CH3 - H CH3 Q-l N CH3 6-OCF~H - H CH3 Q~l N C2H5 H - H CH3 Q-l N l-C3H7 H ~ H CH3 10 Q-l N t-C~Hg H _ H CH3 Q-2 S CH3 5-F ~ ~ CH3 Q-2 S CH3 6-Cl ~ ~ CH3 Q-2 S CH3 5-Bc ~ ~ CH3 15 Q-2 S CH3 6-CH3 ~ ~ CH3 Q-2 S CH3 5-OCH3 ~ ~ CH3 Q-2 S CH3 6-OCF2H ~ ~ CH3 Q-2 S C2H5 H ~ ~ CH3 Q-2 S l-C3H7 H ~ ~ CH3 20 Q-2 S t-C~Hg H ~ ~ CH3 Q-2 CH3 5-F ~ ~ CH3 Q-2 CH3 6-Cl ~ ~ CH3 Q-2 CH3 5-Br ~ ~ CH3 25 Q-2 CH3 6-CH3 - ~ CH3 Q-2 CH3 5-OCH3 ~ ~ CH3 Q-2 C~13 6-OCF2H ~ ~ CH3 Q-2 C2H5 H ~ ~ CH3 Q-2 O l-C3H7 H ~ ~ CH3 30 Q-2 O t-C~Hg H ~ ~ CH3 Q-2 N H H ~ CH3 CH3 Q-2 N CH3 5-F _ H CH3 Q-Z N CH3 6-Cl - H CH3 Q-2 N CH3 5-Br - H CH3 ~2;22~7 Table 4 L~ntinued) ~ Rl a~ R3 Xl m.P.(oc) Q-2 N C2H5 H _ H CH3 Q-2 N ~-C3H7 H - H CH3 Q-2 N t-C4H9 H - H CH3 10 Q_3 S - H CH3 ~ CH3 Q-3 S - 6-Cl H - CH3 Q-3 S - 5-Br H - CH3 Q-3 S _ 6-CH3 H ~ CH3 15 Q_3 S - 5-OCH3 H ~ CH3 Q-3 S _ 6-OCF2H H ~ CH3 Q-3 O - ~ CH3 ~ CH3 20 Q_3 O _ 6-Cl H ~ CH3 Q-3 O - 5-Br H - CH3 Q_3 o - 6-CH3 H ~ CH3 Q-3 O - 5-OCH3 H ~ CH3 Q-3 O - 6-OCF2H H ~ CH3 25 Q_3 N - H H CH3 CH3 Q-3 N _ H CH3 H CH3 Q-3 N - 6-Cl H H CH3 Q-3 N - 5-Br H H CH3 30 Q_3 N - 6-CH3 H H CH3 Q-3 N - 5-OCH3 H H C~3 Q-3 N _ 6-OCF2H H H CH3 Q-4 S _ H CH3 ~ CH3 35 Q-4 S - 5-F H ~ CH3 ~2;2~

Table 4 ~continued) O W R Rl R2 R3 ~1 m.P.(oc) Q-4 S - 6-Cl H - CH3 Q-4 S _ 5-B~ H ~ CH3 Q-4 S _ 6-CH3 H ~ CH3 Q-4 S _ 5-OCH3 H ~ CH3 Q-4 S _ 6-OCF2H H ~ CH3 10 Q_4 O _ H CH3 ~ CH3 Q-4 O - 6-Cl H - CH3 Q-4 O - 5-Br H ~ CH3 Q-4 O - 6-CH3 H ~ CH3 15 Q_4 O _ 5-OCH3 H - ~3 Q-4 O - 6-OCF2H H ~ CH3 Q-4 N _ ~ H CH3 C 3 Q-4 N _ H CH3 H CH3 Q-4 N _ 6-Cl H H C~3 Q-4 N - 5-Br H H CH3 Q-4 N _ 6-CH3 H H CH3 Q-4 N _ 6-OCF2H H H CH3 Q-l S CH3 H CH3 Q-l S CH3 5-CF3 ~ ~ CH3 Q-l S CH3 6-CH20CH3 ~ ~ CH3 Q-l S CH3 5-CH2SCH3 ~ ~ CH3 Q-l O CH3 H ~ ~ OCH3 Q-l o CH3 5-CF3o ~ ~ OCH3 Q-l O CH3 6 CH2 3 oc~3 Q-l O CH3 5-CH2SCH3 ~ ~ OCH3 Q-l N CH 5-CF3 - H CH3 Q-l N CH3 6-CH20CH3 - H CH3 Q-l N CH3 5-CH2SCH3 - H CH3 ~;2227~7 Table 4 (continued~

W R Rl R2 R3 1 m~D.(oc) Q-2 S CH3 5-CF3 ~ ~ CH3 Q-2 S CH3 6-CH20CH3 ~ ~ CH3 Q-2 S CH3 5-CH2SCH3 ~ ~ CH3 Q-2 0 CH3 ~ ~ ~ C~3 Q-2 CH3 5-CF3 ~ ~ CH3 Q-2 CH3 6-CH20CH3 ~ - c~3 Q-2 CH3 5-CH2SCH3 ~ ~ CH3 Q-2 N CH3 H _ H CH3 Q-3 S _ 5-CF3H ~ CH3 Q-3 S - 2 H3 H ~ CH3 Q-3 S _ 5 CH2SCH3 H ~ CH3 Q-3 0 - 5-CF3 H ~ CH3 20 Q_3 0 _ 6 CH2CH3 H ~ CH3 Q-3 0 - 5-CH2SCH3 H ~ CH3 Q-3 N _ 5-CF3 H H CH3 Q-3 N _ 6-CH20CH3 ~ H CH3 25 Q-3 N _ 5 CH25CH3 H H CH3 Q-4 S _ 5-CF3 H ~ CH3 Q-4 S _ 6 CH2CH3 H ~ CH3 Q-4 S _ 5 CH2SCH3 H ~ CH3 Q-4 0 - 5-CF3H ~ CH3 30 Q_4 0 - 6-CH20CH3H ~ CH3 Q-4 0 - 5-CH25CH3H ~ CH3 Q-4 N _ 5-CF3H H CH3 Q-4 N _ 6 CH2CH3 H H CH3 35 Q-4 ~ - 5-CH2SCH3 H H CH3 ~22~

Table 5 N
QS02NEICNH~O~_~
O ~Y

Q W R 1 2 3 1 Y2 m.P. (~C~
Q-l S H H ~ ~ CH3 H
Q- 1 S CH3 5 -F ~ - CH3 H
Q- 1 S CH3 6 - C 1 ~ ~ CH3 H
Q- 1 S CH3 5-Bc ~ ~ C 3 El Q- 1 S CH3 6 - CH3 ~ ~ CH3 CH3 Q- 1 S CH3 5 -OCH3 ~ ~ CH3 CH3 Q- 1 S CH3 6 -OCF2H ~ ~ CH3 CH3 O- l S C2H5 H ~ ~ CH3 H
Q- 1 S i_C3H7 H ~ ~ CH3 H
Q- 1 S t-C4Hg H ~ ~ CH3 CH3 2 Q_ 1 S CH3 H ~ ~ OCH3 H
Q- 1 S CEI3 H _ _ CH2cH3 H
Q-l S CH3 H _ _ OCF2H H

;2-1 O CH3 5-F _ _ OCH H
2 5 Q_ 1 O CH3 6-Cl ~ ~ OCH3 H
Q-1 O CH3 S-B~ ~ ~ OCH3 H
Q- 1 O CH3 6-CH3 ~ ~ OCH3 CH3 Q- 1 O CH3 5-OCH3 ~ ~ OCH3 CH3 Q- 1 O CH3 6 -OCF2H ~ ~ OCH3 CH3 Q- 1 O C2H5 H ~ ~ OCH3 CEI3 Q- 1 O i_C3H7 H ~ ~ OCH3 CH3 Q- 1 O t -C4Hg H ~ ~ OCH3 C~3 Q- 1 N CH3 5-F - H C)CH3 E~

Q- 1 N CH3 6-Cl - H OCH3 E~

Table 5 (continued?

Q W R ~1 R2 R3 ~1 Y2 P- (C) Q- 1 N CH3 S-Br - H OCH3 H
Q-l N CH3 6-CH3 - H OCH3 H
Q-l N CH3 S-OCH3 - H OCH3 H
Q-l N CH3 6-OCF2H - 3 3 Q-l N C2H5 H _ H OCH3 CH3 Q 1 N i C H H _ H OCH3 CH3 Q-l N t-C4H9 H _ H OCH3 CH3 Q~2 S CH3 5-F ~ ~ CH3 H
Q-2 S CH3 6-Cl ~ ~ CH3 H
Q-2 S CH3 5-B~ ~ ~ CH3 H
Q-2 S CE~3 6-CH3 ~ ~ CH3 H
Q-2 S CH3 5-OCH3 ~ ~ CH3 H
Q-2 S CH3 6-OCF2H ~ ~ CH3 CH3 Q-2 S C2H5 H ~ ~ CH3 CH3 Q-2 S i_C3H7 H ~ ~ C~3 CH3 20 Q-2 S t-C4Hg H ~ ~ CH3 C~3 Q-2 O H H ~ ~ CH3 CH3 Q-2 O CH3 5-F ~ ~ CH3 CH3 Q-2 O CH3 6-Cl ~ ~ CH3 CH3 Q-2 O CH3 5-Br ~ ~ CH3 CH3 O
Q-2 CH3 6-CH3 ~ ~ CH3 C~3 Q-2 O CH3 5-OCH3 ~ ~ c~3 H
Q-2 O CH3 6-OCF2H ~ ~ CH3 H
Q-2 O C2H5 H ~ ~ CH3 H
Q-2 O l-C3H7 H ~ ~ CH3 H
30 Q-2 O t-C4Hg H ~ ~ CH3 H
Q-2 N H H ~ 3 3 H
Q-2 N CH3 5-F _ H CH3 H

Q-2 N CH3 6-Cl - H CH3 H
Q-2 N CH3 5-Br _ H CH3 H

~222~7 Table 5 (continueda Q W R Rl R2 ~3 Xl Y2 m.p.~C) Q-2 N C2H5 H _CH3 CH3 Q-2 N i_C3H7 H - 3 3 Q-2 N t-C4H9 H _ H3 CH3 Q-3 S _ ~ H _H3 CH3 Q-3 S _ H CH3 -3 CH3 Q-3 S _ 5-F H _3 CH3 Q-3 S _ 6-Cl H _H3 CH3 Q-3 S - 5-Br H _CH3 CH3 Q-3 S _ 6-CH3 H ~3 H
15 Q_3 S _ 5-OCH3 H _H3 H
Q-3 S _ 6-OCF2H H _CH3 H

Q-3 0 - H CH3 ~ 3 H

20 Q_3 ~ _ 6-Cl H _C~3 H
Q-3 O - 5-B~ H _CH3 CH3 ~ J -- V--~_An 3 ~_L~3 Q-3 O - 5-OCH3 H _CH3 CH3 Q-3 N _ H CH3 ~ 3 3 Q-3 N _ 5-F . H HCH3 CH3 Q-3 N _ 6-Cl H HCH3 CH3 Q-3 N - 5-B~ H HCH3 H
30 Q_3 N _ 6-CH3 H H 3 Q-3 N _ 5-OCH3 H HCH3 H
Q-3 N _ 6-OCF2H H HCH3 ~2Z~7 Table 5 (continuedL

Q W R Rl ~2 R3 Xl Y2 m.P.(~C) Q-4 5 - 6-Cl H - CH3 H
5 Q_4 S - 5-Br H ~ CH3 CH3 Q-4 S _ 6-CH3 H ~ CH3 CH3 Q-4 S _ 5-OCH3 H ~ CH3 CH3 Q-4 S _ 6-OCF2H H ~ CH3 CH3 Q-4 0 - H H ~ CH3 CH3 10 Q_4 o - H CH3 ~ CH3 CH3 Q-4 O - 5-F H ~ CH3 CH3 Q-4 0 - 6-Cl H ~ CH3 CH3 Q-4 O - 5-~r H - CH3 H
Q-4 0 - 6-CH3 H ~ CH3 H
15 Q_4 O - 5-OCH3 H ~ CH3 H
Q-4 O - 6-OCF2H H ~ CH3 H
Q 4 N _ H H CH3 CH3 H
Q-4 N _ H CH3 H CH3 H

20 Q_4 N - 6-Cl H H CH3 H
Q-4 N - 5-~3r H H CH3 CH3 Q-4 N _ 5-OCH3 H H CH3 CH3 Q-4 N _ 6-OCF2H H H CH3 CH3 25 Q-l S CH3 H_ ~ ~ CH3 H

Q-l S CH 6-CH OCH ~ ~ CH3 CH3 Q-l S CH 5-CH SCH ~ ~ CH3 CH3 Q-l O CH3 5-CF3 - - H3 3 30 Q-l O CH 6-CH OCH _ _ OCH3 CH3 Q-l O CH3 5-CH2scH3 - - 3 3 Q-l N CH3 5-CF3 H 3 3 Q-l N CH3 6-CE12OCH3 _ H 3 3 Q-l N CH 5-CH SCH - 3 3 Table_ ~continued~

Q W R Rl R2 R3 ~1 Y~ m.~.LC) Q-2 S CH3 H _ _ CH3 CH3 Q-2 5 CH3 6-CH2CH3 - ~ 3 3 Q-2 O CH3 H _ _ CH3 H

Q-2 0 CH3 6-CH2OCH3 _ _ CH3 H
Q-2 O CH3 5-CH2SCH3 _ _ CH3 H

Q-2 N CH3 5-CF3 ~ H CH3 H

~-2 N CH3 5-CH2SCH3 - H CH3 Q-3 S _ 5-CF3 H _ CH3 H
Q-3 S _ 6-CH20CH3 H _ CH3 H
Q-3 S _ 5-CH2SCH3 H _ CH3 H
Q-3 0 - 5-CF3 H _ CH3 CH3 20 Q_3 O _ 6-CH2OCH3 H - 3 3 Q-3 O - 5-CH2SCH3 H _ CH3 CH3 Q-3 N _ 5-CF3 H H 3 Q-3 ~ - 6-CH2OCH3 H H CH3 H
25 Q_3 N - 5-CH2SCH3 H H CH3 H
Q-4 S _ 5-CF3 H _ CH3 CH3 Q-4 S _ 6-CH2OCH3 H _ CH3 CH3 Q-4 S _ 5-CH2SCH3 H ~ CH3 H3 Q-4 0 - 5-CF3 H _ C 3 H
30 Q_4 o - 6-CH2OCH3 H - 3 Q-4 O - 5-CH2SCH3 H _ CH3 H
Q-4 N _ H H H CH3 CH3 Q-4 N _ 6-CH2OCH3 H H CH3 CH3 J~

Table 6 N N'Y3 QS02NHCNH~/ I
O N_~ X2 Q W R Rl R2 R3 X2 Y3 m.P.(C
Q-l S H H ~ ~ CH3 CH3 10 Q-l S CH3 H ~ CH3 CH3 Q-l S CH3 H _ _ OCH3 CH3 Q-l S CH3 H _ _ SCH3 CH3 Q-l S CH3 5-F ~ ~ CH3 CH3 Q-l S CH3 6-C1 ~ ~ CH3 CH3 15 Q-l S CH3 5-Br ~ ~ CH3 CH3 Q-l S CH3 6-CH3 ~ ~ CH3 CH3 Q-l S CH3 5-OCH3 ~ ~ CH3 CH3 Q-l S CH3 6-OCF2H ~ ~ CH3 CH3 Q-l S CH3 5-CF3 ~ ~ CH3 CH3 20 Q-l S CH3 6-CH2OCH3 ~ ~ CH3 CH3 Q-l S CH3 5-CH2SCH3 ~ ~ CH3 C~3 Q-l S C2H5 H ~ ~ CH3 CH3 Q-l S i-C3H7 H - ~ CH3 CH3 Q-1 S t-C H~ H ~ ~ CH3 CH3 25 Q-l O H H ~ - CH3 CH3 Q-l O CH3 H ~ ~ CH3 CH3 Q-l O CH3 5-F ~ ~ CH3 CH3 Q-l O CH3 6-Cl ~ ~ CH3 CH3 Q-l O CH3 5-Br ~ ~ CH3 CH3 30 Q-l O CH3 6-CH3 ~ - CH3 CH3 Q-l O CH3 5-OCH3 ~ ~ CH3 CH3 Q-l O CH3 6-OCF2H ~ ~ CH3 CH3 Q-l O CH3 5-CF3 ~ ~ CH3 CH3 Q-l O CH3 6-CH2OCH3 ~ ~ CH3 CH3 35 Q-l O CH3 5-CH2SCH3 ~ ~ CH3 CH3 122Z~

13bl~ A C ~

Q W R 1 2 3 2 3 m.v.(C) Q-1 O C2H5 H ~ ~ 3 3 Q-1 O i-C3H7 H _ _CH3 CH3 Q-1 O t-C4Hg H - - 3 3 Q-1 N H H _ CH3 CH3 CH3 Q-1 N H CH3 ~ H3 H3 Q-1 N CH3 H _ HCH3 CH3 Q-1 N CH3 5-Br _ HCH3 CH3 Q-1 N CH3 6-C~3 - 3 3 Q-1 N C2H5 H _ HCH3 CH3 Q-1 N i-C3H7 H _ HCH3 CH3 Q-1 N t-C4Hg H _ HCH3 CH3 Q-2 S H H _ _CH3 C~3 Q-2 S CH3 E~ _ _CH3 CH3 Q-2 S CH3 5-F - ~ 3 3 Q-2 S CH3 6-C1 - ~ 3 3 Q-2 S CH3 5-Br - - CH3 3 Q-2 S CH3 6-CH3 _ _CH3 CH3 Q-2 S CH3 5-OCH3 - ~ 3 3 Q-2 S C2H5 H ~ ~ 3 3 Q-2 S i_C H H ~ ~ 3 3 Q-2 S t-C4Hg H - ~ 3 3 ~2;227~

Table 6 tcontinued) Q ~ R Rl R2 R3 X2 Y3 m.P.(9c) Q-2 O H H _ _CH3 CH3 Q-2 O CH3 H _ _H3 CH3 Q-2 O CH~ s-F - ~3 3 Q-2 O CH3 6-Cl - - 3 3 Q-2 O CH3 5-Br - _3 CH3 Q-2 O CH3 6-CH3 -CH3 CH~

Q-2 O C2H5 H _ _CH3 CH3 Q-2 O i-C3H7 H _ _CH3 CH3 Q-2 O t-C4H~ H _ _CH3 CH3 Q-2 N H H _CH3 CH3 CH3 2 Q-2 N CH3 H _ HCH3 CH3 Q-2 N CH3 5-F _ HCH3 CH3 Q-2 N CH3 6-Cl - 3 3 Q-2 N CH3 5-Br _ HCH3 CH3 Q-2 N CH3 6-CH3 _ CH3 C 3 Q-2 N i_C H H ~ ~ 3 3 Q-2 N t-C4Hg H - 3 3 Q-3 S _ H H _ CH3 CH3 Q-3 S _ H CH3 - 3 3 Table 6 (continued~

W R 1 2 32 3 m.~.(C) Q-3 S - 6-Cl H _ CH3 CH3 5 Q-3 S - 5~ _ CH3 C~3 Q-3 S - ~-CH H - CH3 CH3 Q-3 S - s-CF3 H - 3 3 10 Q_3 S - 6-CH20CH3 H ~ 3 3 Q-3 S - 5-CH2SCH3 H _ CH3 CH3 Q-3 0 - H H _CH3 CH3 15 Q-3 o - 6-Cl H _H3 C 3 Q-3 0 - 5-Br H - 3 3 Q-3 0 - 6-CH3 H _CH3 CH3 Q-3 0 - 5-OCH3 H _CH3 CH3 Q-3 0 - 6-OCF2H H _CH3 CH3 20 Q-3 o - 5 CF3 H - 3 3 Q-3 o - 6-CH20CH3 H - 3 3 Q-3 o - 5-C~2SCH3 H - 3 3 25 Q_3 N - H H H 3 3 Q-3 N - 6-Cl H H 3 3 Q-3 N - 5-Br H H 3 3 ~_3 N - 5-OCH3 H HCH3CH3 Q-3 N - 5-C~3 H H 3 3 ~227~
0o Table 6 (conti_ued) Q W R ~ R2 R3 X2 Y3 m.P.(C) Q-4 S - H H _ CH3 C2H5 Q-4 S - 5-F H_CH3 C2H5 Q-4 S - 6-Cl H_CH3 C2H5 Q-4 S - 5-Br H_CH3 C2H5 Q-4 S - 6-CH3 H_CH3 C2H5 Q-4 S - 5-OCH3 H _ CH3 C2H5 Q-4 S - 6-OCF2H H _ CH3 C2H5 Q-4 S - 5-CF3 H_CH3 C2H5 Q-4 S - 6-CH2OCH3 H _ CH3 C~H5 Q-4 S - 5-CH2SCH3 H_CH3 C2H5 Q-4 O - H H_CH3 C2H5 Q-4 O - 5-F H_ CH3 C2H5 Q-4 O - 6-Cl H - CH3 C2H5 Q-4 O - 6-CH3 H_ 3 2 5 Q-4 O - 5-OCH3 H _ CH3 C2H5 Q-4 O - 6-OCF2H H _ CH3 C2H5 Q-4 O - 5-CF H_ CH3 C2H5 Q-4 N - 6-Cl HH CH3 CH2CF3 Q-4 N - 5-Br HH CH3 CH2CF3 Q-4 N - s-CF3 HH CH3 CH2CF3 274~
~1 Table 6 ~continued~

V ~I R 1 R2 3 ~2 3 m.P.(~C~

~2~

Table 7 N ( QS02NHCNH-CH2~( O N
O N--~

Q ~ R R1 R2 R3 X3 m P (C) Q 1 S CH3 H ~ ~ CH3 Q-1 S CH3 5-F ~ ~ CH3 Q-1 S CH3 6-C1 ~ ~ CH3 Q- 1 S CH3 5-Br ~ ~ CH3 Q-1 S CH3 6-CH3 ~ ~ CH3 Q- 1 S CH3 5-OCH3 ~ ~ CH3 Q- 1 S CH3 S-OCF2H ~ ~ CH3 Q-1 S CH3 5-CF3 ~ ~ C~3 Q-l S CH3 5-CH2SCH3 ~ ~ CH3 Q-1 S ~2H5 H ~ ~ C~3 Q-l S 1-C3H7 H - - CH3 Q-1 S t-C~H9 H CH3 Q-1 S CH3 H ~ ~ OCH3 25 Q-1 O H H ~ ~ CH3 Q-1 CH3 H ~ ~ CH3 Q-1 CH3 5-F ~ ~ CH3 Q-1 CH3 6-C1 ~ ~ CH3 Q-1 O CH 5-Br CH3 30 Q-1 CH3 6-CH3 ~ ~ CH3 Q 1 C~3 5-OCH3 ~ ~ CH3 Q- 1 CH3 6-OCF2H ~ ~ CH3 Q-l CH3 5-CF3 ~ ~ C~3 Q-1 CH3 6-CH20CH3 ~ ~ CH3 Q-1 CH3 5-CH2SCH3 ~ ~ CH3 ~2 ~L222747 Table 7 (continued~

Q ~ R Rl R2 R3 X3 m.P.( Q-l C2~ H ~ ~ CH3 5 Q-l o 1 C3H7 H CH3 Q-l O t-C4Hg H ~ ~ CH3 Q-l N H H ~ CH3 CH3 Q-l N H H - H CH3 10 Q-l N CH3 H _ H CH3 Q-l N CH3 5-F _ H CH3 Q-l N CH3 6-Cl - H CH3 Q-l N CH3 5-Br _ H CH3 Q-l N CH3 6-CH3 - H CH3 15 Q-l N CH3 5-OCH3 - H CH3 Q-l N CH3 6-OCF2H - H CH3 Q-l N CH3 5-CF3 - H CH3 Q-l N CH3 2 3 H CH3 Q-l N CH3 5-CH25CH3 - H CH3 20 Q-l N C2H5 H - H CH3 Q-l N i-C3H7 H _ H CH3 Q-l N t-C4Hg H _ H CH3 Q-l M CH3 H _ H OCH3 25 Q-2 S CH3 H ~ ~ CH3 Q-2 S CH3 5-F ~ ~ CH3 Q-2 S CH3 6-Cl ~ ~ CH3 Q-2 S CH3 5-Br ~ ~ CH3 Q-2 S CH3 6-CH3 ~ ~ CH3 30 Q-2 S CH3 5-OCH3 ~ ~ CH3 Q-2 S CH3 6-OCF2H ~ ~ CH3 Q-2 S CH3 5-CF3 ~ ~ CH3 Q-2 S CH3 6-CH2OCH3 ~ ~ CH3 Q-2 S CH3 5-CH2SCH3 ~ ~ CH3 35 Q-2 2 5 H ~ ~ CH3 8~
Table 7 ~c~n~inued) Q W ~ Rl R2 R3 ~3 m.P.(C3 Q-2 S i_C3H7 H ~ ~ CH3 5 Q-2 S t-C4H~ H ~ ~ CH3 Q-2 S CH3 H ~ - OCH3 Q-2 CH3 H ~ ~ CH3 Q-2 CH3 S-F ~ ~ CH3 10 Q-2 ~H3 6-Cl ~ ~ CH3 Q-2 CH3 5-Br ~ ~ CH3 Q-2 CH3 6-CH3 ~ ~ CH3 Q-2 CH3 5-OCH3 ~ ~ CH3 Q-2 CH3 6-OCF2H ~ ~ CH3 15 Q-2 CH3 5-CF3 ~ ~ CH3 Q-2 CH3 6-CH2OCH3 ~ ~ CH3 Q-2 CH3 5-CH2SCH3 ~ ~ CH3 Q-2 C2H5 H ~ ~ CH3 Q-2 O l_C3H7 H ~ ~ CH3 20 Q-2 O t-C4Hg H ~ ~ CH3 Q-2 CH3 H ~ ~ OCH3 Q- 2 N H H -~ CH3 CH3 Q-2 N CH3 H _ H CH3 Q-2 N CH3 5-F _ H CH3 Q-2 N CH3 6-Cl - H CH3 Q-2 N CH3 5-Br - H CH3 Q-2 2 5 H _ H CH3 Q-2 N i_C H7 H _ H CH3 2~

Table 7 (continued) Q W R 1 2 3 3 m.P.(C
Q-2 N ~-C4Hg H ~ H CH3 5 Q-2 N CH3 H _ H OCH3 Q-3 S _ H CH3 ~ CH3 Q-3 S - 6-Cl H - CH3 10 Q_3 S - 5-BI H ~ CH3 Q-3 S _ 6-CH3 H ~ CH3 Q-3 S _ 5-OCH3 H ~ CH3 Q-3 S _ 6-OCF2H H ~ CH3 Q-3 S _ 5-CF3 H ~ CH3 15 Q_3 S - 6-CH2OCH3 H ~ CH3 Q-3 S _ 5-CH2SCH3 H ~ CH3 Q-3 O - H CH3 ~ CH3 20 Q_3 O _ 5-F H ~ CH3 Q-3 O - 6-Cl H - CH3 Q-3 O - S-Br H - CH3 Q-3 O - 6-CH3 H ~ CH3 Q-3 O - 5-OCH3 H ~ CH3 25 Q_3 0 _ 6-OCF2H H ~ CH3 Q-3 o - 5-CF3 H ~ CH3 Q-3 O - 6-CH2OCH3 H ~ CH3 Q-3 o - 5-CH2SCH3 H ~ CH3 30 Q_3 N - H H 3 3 Q-3 N _ H CH3 H CH3 Q-3 N - 5-~ H H CH3 35 Q-3 N - 5-Br H H CH3 Table 7 (continued) W R 1 R2 3 ~3 m.P.(oc) Q-3 N _ 6-CH3 H H CH3 2-3 N _ 6-OCF2H H H CH3 Q-3 N _ C 2 3 H H CH3 Q-3 N _ 2 3 H H CH3 Q-4 S _ H CH3 ~ CH3 Q-4 S - S-Cl H - CH3 15 Q_4 S _ 5-Br H ~ CH3 Q-4 S _ 6-CH3 H ~ CH3 Q-4 S _ 5-OCH3 H ~ CH3 Q-4 S _ 6-OCF2H H ~ CH3 Q-4 S _ 5-CF3 H ~ CH3 Q-4 S _ 6 CH2 3 H ~ CH3 Q-4 S _ 2 3 H ~ CH3 0-4 O - H CH3 ~ CH3 25 Q_4 O - 5-F H ~ CH3 Q-4 O - 6-Cl H - CH3 Q-4 O - 5-Br H - CH3 Q-4 o - 6-CH3 H ~ CH3 Q-4 O - 5-OCH3 H ~ CH3 Q-4 O - 6-OCF2H H ~ CH3 Q-4 O - 5-CF3 H ~ CH3 Q-4 O - 6-CH20CH3 H ~ CH3 Q-4 O - 5-CH2SCH3 H ~ CH3 Q-4 O - H H ~ OCH3 Q-4 N _ H H CH3 CH3 ~2~27~7 ~7 Table 7 ~continuedL

W a 1 2 3 3 m . P . ( C 2 Q- 4 N _ H CH3 H CH3 Q-4 N - 6-Cl H H CH3 Q-4 N - 5-Br H H CH3 Q- 4 N _ 6 -CH3 H H CH3 Q- 4 N _ 5 -OCH3 H H CH3 Q- 4 N _ 6-OCFi!H H H CH3 Q-4 N _ 5-CF3 H H CH3 Q-4 N _ 5-CH2SCH3 H H CH3 88 7~
Table 8 QSO2NHCNH ~ Z
O M ~

Q W R Rl R2 ~3 ~4 Y4 Z (C) 10 Q-l S H H - - CH3 CH3 CH
Q-l S CH3 H - - CH3 CH3 N
Q-l S CH3 H - - CH3 CH3 CH
Q-l S CH3 H - - OCH3 CH3 CH
Q-l S CH3 CH2CH3 CH3 CH
15 O-l S CH3 H- - CH2OCH3 CH3 CH
Q-l S CH3 H - - Cl CH3 CH
Q-l S CH3 H - - CH3 OCH2CH3 CH
Q-l S CH3 H - - CH3 OCH3 CH
Q-l S CH3 H - - CH3 Cl CH
20 Q-l S CH3 5-F - - CH3 CH3 CH
Q-l S CH3 6-Cl - - CH3 CH3 CH
Q-l S CH3 5-B~ - - CH3 CH3 CH
Q-l S CH3 6-CH3 - - CH3 CH3 CH
Q-l S CH3 5-OCH3 - - CH3 c~3 CH
25 Q-l S CH3 6-OCF2H - - CH3 CH3 CH
Q-l S CH3 5-CP3 - - CH3 CH3 CH
Q-l S CH3 6-CH2CH3 ~ C 3 CH3 CH
Q-l S CH3 5-CH2SCH3 - - CH3 c~3 CH
Q-l S C2H5 H - - CH3 CH3 CH
30 Q-l S i-C3H7 H - - CH3 CH3 CH
Q-l S t-C4Hg H - - CH3 CH3 CH
Q-l O CH3 H - - CH3 CH3 CH
Q-l O CH3 5-F - - CH3 CH3 CH
Q-l O CH3 6-Cl - - CH3 CH3 CH
35 Q-l O CH3 5-B~ - - CH3 CH3 CH

~8 ~2;2279~7 Table 8 (continued) Q W R Rl R2 R3 X4 Y4 z m.P.(C) Q ,CH3 5 OCH3 CH3 CH3 CH
Q-l O CH3 6-OCF2H - - CH3 CH3 CH

Q-l O CH3 6-CH20CH3 - - CH3 CH3 CH
Q-l O CH3 5-CH2SCH _ _ CH3 CH3 CH
Q-l N H H - CH3 CH3 CH3 CH
Q-l N H H - H CH3 CH3 CH
Q-l N CH3 H - H CH3 CH3 CH
Q-l N CH3 5-F - H CH3 CH3 CH
Q-l N CH3 6-Cl - H CH3 CH3 CH
15 Q-l N CH3 5-Br - H CH3 CH3 CH
Q 3 3 ~ H CH3 CH3 CH

Q-l N CH3 6-OCF2H - H CH3 CH3 CH
Q CH3 5 CF3 _ H CH3 CH3 CH
Q-l N CH3 6-CH20CH3 - H CH3 CH3 CH
Q-l N CH3 5-CH2SCH3 - H CH3 CH3 CH
Q-2 S CH3 H _ _ CH3 CH3 CH

Q-2 S CH3 6-Cl ~ ~ CH3 CH3 CH
Q-2 S CH3 S-Br - - CH3 CH3 CH

Q-2 S CH3 6-OCF H _ _ CH3 CH3 CH

Q-2 O CH3 6-Cl _ _ CH3 CH3 CH
35 Q-2 O CH3 5-B~ ~ CH3 CH3 CH

~27~7 Table 8 (continued) Q W R Rl R2 R3 X4 Y4 z ( C) Q 2 O CH3 6 C~3 CH3 CH3 CH
Q-2 0 CH3 5-OCH3 ~ ~ CH3 CH3 CH
Q-2 O CH3 6-OCF2H _ _ CH3 CH3 CH

Q-2 O CH3 6-CH2OCH3 _ _ CH3 CH3 CH

Q-2 N H H _ H CH3 CH3 CH
Q-2 N CH3 H _ H CH3 CH3 CH

Q-2 N CH3 6-Cl - ~ CH3 CH3 CH
15 Q-2 N CH3 5-Br - H CH3 CH3 CH

Q-3 S _ H CH3 -CH3 CH3 CH
Q-3 S _ H H -CH3 CH3 CH
Q-3 S _ 5-F H _CH3 CH3 CH
25 Q-3 S - 6-Cl H _CH3 CH3 CH
Q-3 S _ 5-Br H _CH3 CH3 CH
Q-3 S _ 6-CH3 H _CH3 CH3 CH
Q-3 S _ 5-OCH3 H _ CH3 CH3 CH
Q-3 S _ 6-OCF2H H _ CH3 CH3 CH
30 Q-3 S - 5-CF3 H _CH3 CH3 CH
Q-3 S _ 6-CH2OCH3 H - CH3 CH3 CH
Q-3 S _ 5-CH2SCH3 H - CH3 CH3 CH
Q-3 0 - H H _ CH3 CH3 CH

Q-3 O - 5-F H _ CH3 CH3 CH

7~7 Table 8 ~continued) Q ~ R Rl R2 R3 X4 y4 z Q-3 O - 6-Cl H_ CH3 CH3 CH
Q-3 O - 5-Br H_ CH3 CH3 CH
Q-3 O - 6-CH3 H_ CH3 CH3 CH
Q-3 O - 5-OCH3 H _ CH3 CH3 CH
Q-3 O - 6-~CF2H H _ CH3 CH3 CH
Q-3 O - 5-CF3 H_ CH3 CH3 CH

~_3 ~ - H 33 CH3 CH

Q-3 N - 6-Cl HH CH3 CH3 CH
Q-3 N - 5-Br HH CH3 CH3 CH

Q-3 N - s-CF3 HH CH3 CH3 CH

Q-4 S - H H_CH3 CH3 CH
Q-4 S - 5-F H_CH3 CH3 CH
Q-4 5 - 6-Cl H_CH3 CH3 CH
Q-4 S - 5-Br H_CH3 CH3 CH
Q-~ S - 6-CH3 H_CH CH CH

Q-4 S - 5-OCH3 H_CH3 CH3 CH

Q-4 S - 6-OCF2H H_CH3 CH3 CH
Q-4 S - 5-CF3 H_CH3 CH3 CH

~22~7~7 Table 8 (continued~

Q W R Rl R2 R3 ~4 ~ Z m.~.~C) Q-4 0 - ~ H _CH3 CH3 CH
Q-4 0 - 5-F H _CH3 CH3 CH
Q-4 O - 6-Cl H _CH3 CH3 CH
Q-4 - 5-Br H _CH3 CH3 CH
Q-4 o - 6-CH H _CH3 CH3 CH
Q-4 0 - 5-OCH3 H _ CH3 CH3 CH
Q-4 O - 6-OCF2H H _ CH3 CH3 CH
Q-4 0 - 5-CF H _CH3 CH3 CH

Q_4 N - H 3 CH3 CH3 CH

Q-4 N - 6-Cl H H CH3 CH3 CH
20 Q_~ N - 5-Br H H CH3 CH3 CH

25 Q_4 N - 6-CH2OCH H H CH3 CH3 CH

~7~7 ~%~

Formulations Useful formulation6 of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, 6uspen6ions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly.
Sp~ayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compoçitions are primarily used as intermediates for further ormulation. The formulations, broadly, con-tain about 1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfac-tant(s) and (b) about 5~ to 99% solid or liquid diluent(s). More specifically, they will contain these ingredient6 in the following approximate propor-tions:
Percent by Weight Active Inqredient Diluent(6~ Surfactant(s) Wettable Powders20-90 0-74 1-10 Oil Suspensions,5-50 40-95 0-15 Emulsions, Solutions, (including Emulsifiable 25 Concentrates) Aqueous Suspension 10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granule~ and Pellets 1-95 5-99 0-15 High Strength 90-99 0-10 0-2 30 Compositions Lower or higher levels of active ingredien~ can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are some-times de6irable, and are achieved by incorporationinto the formulation or by tank mixing.

7~

~4 Typical solid diluents are de~cribed in Watkins, et al., "Handbook of Insecticide Du~t Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other 601ids, either mined or manufac-tured, may be u~ed. The more absorptive diluent~ areprefer~ed for wettable powders and the denEeI one6 for dusts. Typical liquid diluents and 601vent6 are de-6cribed in Mar6den, "Solvents Guide," 2nd Ed., Inter-6cience, New York, 1950. Solubility under 0.1% i6 preferred for 6uspension concentrates; 601ution con-centrates are preferably stable against phase ~epara-tion at O~C. "McCutcheon'~ Detergent6 and Emul6ifier6 Annual", MC Publi~hing Corp., Ridgewood, New Je~6ey, a6 well a6 Si~ely and Wood, "Encyclopedia of Surface Active Agent6", Chemical Publishinq Co., Inc., New ~ork, 1964, li~t 6urfactants and recommended u6e6.
All formulations can contain minor amount6 of addi-tive6 to reduce foam, caking, corro6ion, microbio-logical growth, etc. Preferably, ingredients ~hould be approved by the U.S. Environmental Protection Agency for the u~e intended.
The methods of making 6uch compositions are well known. Solution6 are prepared by 6imply mixing the ingredient~. Fine ~olid compo6itions are made by blending and, u~ually, grinding as in a hammer or fluid energy mill. Su6pen~ions are prepaIed by wet milling (see, for example, Littler, U.S. Patent 3D060~084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E.
Browning, "~gglomeration", Chemical Enqineerinq, December 4, 1967, pp. 147ff. and "Perry'6 Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-59ff.

~2;~:;279~

For further information regarding the art of formulation, ~ee for example:
H. M. Loux, U.S. Patent 3,235,361, February 15, 1966, Col. 6, line 16 ~hrough Col. 7, line 19 and Examples 10 through 41;
R. W. Luckenbaugh, U.S. Patent 3,309,192, March 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Example6 8, 12, 15, 39, 41, 52, 53, 58, 132, 13B-140, 162-164, 166, 167 and 169-182:
H. Gy6in and E. Knusli, U.S. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Example6 1-4;
G. C. ~lingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96;
J. D. Fryer and S. A. Evan6, "Weed Control Hand-book", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103;
J. B. Buchanan, U.S. Patent 3,576,834, April 27, 1971, Col. 5, line 36 through Col. 7, line 70 and Examples 1-4, 17, 106, and 123-140:
R. R. Shaffer, U.S. Patent 3,560,616, February 2, 1971, Col. 3, line 48 through Col. 7, line 26 and Examples 3-9 and 11-18; and E. Somer6, "Formulation", Chapter 6 in Torgeson, "Fungicide6", Vol. I, Academic Press, New York, 1967.
In the following examples, all parts are by weight unles6 otherwise indicated.
ExamPle 11 Wettable Powdec N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methyl-4-benzothiazolesulfonamide 80%
sodium alkylnaphthalene6ulfonate 2%
60dium ligninsulfonate 2%
6ynthetic amorphou6 silica3%
kaolinite 13~
The ingredients are blended and hammermilled.

~Z27~7 ExamPle 12 Hiah Strenqth Concentrate N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]--2-methyl-4-benzothiazolesulfonamide 95.%
S silica aerogel 0.5S
synthetic a~orphou6 fine silica 4.5%
The ingredient6 are blended and ground in a hammer mill to produce a high strength concentrate essentially all pa66ing a U.S.S. No. 50 6creen (0.3 mm openings). Thi6 material may then be formulated in a variety of way6.
ExamPle 13 Du6t wettable powder of Example 11 10%
pyrophyllite (powder) 90%
The we~table powder and the pyrophyllite diluent are thoroughly blended and then packaged. ~he product i8 ~uitable for use as a du6t.
EXalilPle 14 Granule Wettable Powder of Example 11 80~
6ugar 20%
The ingredient6 are blended in a rotating or fluid bed mixer and water sprayed on to accompli~h granulation. When most of the material has reached the de~ired range of 1.0 to 0.42 mm (U.S.S. #18 ~o 40 6ieve~), the granule6 are removed, dried, and screened.
over6ize material is crushed to produce additional material in the desired range. These granules contain 64% active ingredient.

a ExamPle 15 Solution N-[(4-methoxy-6-me~hylpyrimidin-2-yl~aminocarbonyl]-2-methyl-4-benzo~hiazolesulfonamide 30%
di~ethylformamide 70%
The ingredients are combined and 6tirred to produce a solution. which can be used for low volume applications.
Example 16 Emulsifiable Concentrate N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methyl-4-benzothiazole6ulfonamide, 10%
blend of oil soluble sulfonates and polyoxyethylene ether~ 4 xylene 86 The ingredients are combined and stirred until the active i~ di~601ved. A fine screen filter i6 included in ~ackaging operation to insure the absence of any extraneous undissolved material in the product.
Example 17 Aqueous Suspension N-~(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methyl-4-benzothiazole~ulfonamide 50.1%
dodecylphenol polyethylene glycol ether 0.5~
crude calcium ligninsulfonate 5.0%
xanthan gum thickener 0.2%
paraformaldehyde 0.2%
water 44%
The ingredients are ground together in a sand, ball or colloid mill to produce particles essentially all under 5 microns in 6ize.

~2~
7~7 Utility Test re6ults indicate that the compounds of the eresent invention are highly active preemergent or postemergent herbicides or plant growth regulant~.
Many of them have utility for broad-6pectrum pre-andtor post-emergence weed control in areas where complete control of all vegetation is desired, 6uch as around fuel storage tanks, ammunition depots, indus-~rial s~orage area~, parking lots, drive-in theaters, around billboards, highway and railroad structures.
Some of the compound~ have utility for selective weed control in crop~ such as rice, wheat, and barley.
Alternatively, the subject compound6 are useful to modify plant growth.
The rates of application for the compound~ of the invention are d~termined by a number of factors, including their use a6 plant grow~h modifier6 or as herbicides, the crop species involved, the type~ of weeds to be controlled, weather and climate, formu-lations selected, mode of application, amount of foliage pre6en~, etc. In general term6, the subject compound6 should be applied at levelfi of around 0.05 to 10 kg/ha, the lower rate~ being ~ugge6ted for u6e on lighter soil6 and/or tho6e having a low organic matter content, for selective weed control or for situations where only short-term persi6tence i6 required.
The compounds of the invention may be used in combination with any other commercial herbicide;
examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium type6.
The herbicidal properties of the subject compounds were di~covered in a number of greenhouse test~. The te6t procedures and results follow.

Compound ~
~H3 Compound 1 N S OCH3 ~S02NHCONE~

Compou~d 2 . N S O~H3 <~502NHCONH~

N~S OCH
Compound 3 )--( N_( 3 ~ 502NHCONH~
oc~3 C ( CH3 ) 3 ComPound 4 N O OCH3 < ~ S02NHCONH-< ~
c~3 ~Z;;:Z74L~

ComPounds (continuedL
C(CH3)3 COmPOUnd 5 N O OC~I3 ~ S02NHCONH ~ O N

COmPOUnd 6 ~ ~CH3 1 5 SO2NHcONH~
~CH3 S ~N OCH3 COmPOUnd 7 )~--( N__( S02NHCONH~(( ~

~ 3 COmPOUnd 8 S N OCH3 ~ SO2NHCONH-( O N

~LI~ 74~7 ComPounds (continued2 CH

S~N
Com~ound 9 )--( N~CH3 ~ S02NHCONH-< O~>

S~N
Compound 10 )--( oc~3 ~S02NHCONE~) 1~1 , ~2~;27~7 Test A
Seeds of crabgras~ (Diaitaria 5p. ), barnyard-gras6 (~h1~Ehl~ crusaalli3, wild oats ~Avena fatua), ~icklepod (Ca6sia obtusifolia), morningglory 5 ( IPOmOea 8pp. ), cocklebur (~anthium pensylvanicum), 60lghum, corn, soybean, ~ugarbeet, cotton, rice, wheat and purple nut~edge (CvPerus rotundus) tubers were planted and treated pre-emergence with the te~t chemical~ di~solved in a non-phytotoxic ~olvent.
At the same time, the~e crop and weed species were treated with a ~oil/foliage application. At the time of treatment, the plant ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for re6ponse to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompany-ing descriptive symbols have the following meanings:
C = chlorosis/necro6is;
B = burn:
D = defoliation;
E = emergence inhibition;
G = growth retardation:
H = formative effects;
U = unusual pigmentation;
= axillary stimulation;
S = albinism; and 6Y = abscised buds or flowerfi.

lOZ

~ ~ ~ ~ ~ ~ 3 Table A

Compound 1 Compound 2 Rate kg/ha .4 .05 .4 .05 POSTEMERGENCE
Morningglory 3C,9G lC.3G lC 2C
Cocklebur 5C,9G 5C,9G 6C,9G 4C,9G
Sicklepod ~C,9G 3C,3H 3C,9H 3C,7H
Nut6edge lOC 3C,6G 2C,9G 5G
Crabgras6 lC,5G O 2C,3G O
Barnyardgrass 2C,6G O O O
~ild Oat6 2~ 0 0 0 Wheat 2G O O O
Corn lC,3G O 2G O
Soybean 4C,9G 3C,8G 3C,9G 3C,8G
Rice 2C,8G O 3C,5G O
15 Sorghu~ 3C,9H lC 3C,6G O
Sugar beet9C 9C lOC 9C
Cotton 4C,9G 3C,7G 3C,4H,8G 3C,3H,8G
Bu~h bean lC,lH O lC O
PREEMERGENCE
Morningglory 9G O 9G 2H,2C
Cocklebur - 9G 9H 9H
Sicklepod 5C,9G 3C,5G 2C O
Nut~edge 2C,9G O 2C,9G 2G
Crabgrass 2C lC 3G lC
Barnyardgra~ 4C,8H 3C 3C,6G 2C
~ild Oats 2C,8G O 8G 2C
Wheat 5G O 3G O
Corn 2C,8H lC lC,7G 2G
25 Soybean 2C,8H 3C,3G 2C.2H lC
Rice 3C,7G 3C,3G 2C,8H 2G
Sorghum ~ 2C,8H 3G 3C,7G lC
Sugar beet 5C,9G 2C,8G 9C 8G
Cotton ~%~

Table A (continued~

Compound 3 Cmpd. 4 Cmpd. 5 5 Rate kg/ha .4 .05 4 4 POSTEMERGENCE
Morningglory 2C,3H O 2C,7G 2C,9H
Cocklebur2C,9G lH 5C,9G 3C,5G
Sicklepod 2C O 2C,2H 2C
10 Nutsedge O 0 2C,4G O
Crabgras~ O 0 2G 2G
Barnyardgrass O O lH O
Wild Oat~ O O O O
Hheat O O o o Corn lC O lC,2H O
Soybean3C,BG,5X 2C,3H 2C,7H lC,2H
Rice 9G lC,8G ~C,5G 2G
15 SoLghu~ 2C,5H 2C,3G 4G O
Sugar beet 9C 4C.BG 3C,7G 4C,8H
Cotton 3C,3H,7G 2C,2H 2C,3H O
Bush bean 3C,3H,6Y lC lC
PREEMERGENCE
Morningglory 3C,6H O 2C 2C,5H
20 Cocklebur lC,3H O - lC
Sicklepod 3C ~ O
Nutsedge O O O O
Ccabgras6 2G O lC 5G
Barnyardgrass 2C lC 3C lC
Wild Oats 2C O lC 2C
Wheat 3G 0 0 Corn 2C,7G lC 2C,5G 2C
25 Soybean 3C,4H lC lH 2C
Rice 3C,8H 3C 4G 2C
Sorghum 3C,9H 2C,5G 2C,6G 4G
Sugar beet 6C,9G lC,5H 8G 2C,5G
Cotton - - - lC

2~

Tabl2 A ( continued) Cmpd. Cmpd. Cmpd. Cmpd. Cmpd.

Rate kg/ha .05 .05 .05 .05 .05 POSTEMERGENCE
Mocningglory 2C,7G 2C,8G 8H lC 5C,9G
Cocklebur 10C 10C 4C,9G 2G 9C
Sicklepod5C,9G 9C 5C,9G lC 4C,8G
Nutsedge 9C 2C,3G 0 0 2C,9G
Crabgrass 5G 0 0 0 2C,3G
Bacnyardgrass 3C,9H 3H 2H 0 4C,8H
Wild Oats2C,5G 0 0 0 0 Wheat 6G O 0 0 0 Corn 9G 9H 4C,8H 0 2C,9G
Soybean 5C,9G 5C,9G 5C,9G 0 4C,8G
Rice 4C,9G 9C 9C 0 5C,9G
Sorghum 4C,9H 5C,9H 5C,9H 0 4C,9H
Sugar beet10C 9C 9C 3G 5C,9G
Cotton 9C 5C,9G 4C,8& 0 3C,9G
Bu~h bean PREEMERGENCE
~orningglory 8G 6G 5G 2C 9G
Cocklebur 8H 6H 7G 0 8H
Sicklepod2C,9G 6G 7G 0 2C,8G
Nutsedge 8G 0 0 0 8G
Crabgrass2C,4G 0 2C 0 2C,6G
Barnyardgca~s 3C,9H 3C,4G lC 0 5C,9H
Wild Oat~2C,7G 2C 2G 0 5C,9G
Wheat 7G 2C 4G 0 2C,8G
Corn 2C,9G 2C,8G 2C,8H 0 4C,9G
Soybean 2C,7H 3C,5H ~C,6H lC 3C,7G
Rice 10E 4C,8H 9H 0 10E
Sorghum 5C,9H 4C 8H 3C,8H 0 5C,9H
Sugar beet8G 5C,9G 9C 3H 9C
Cotton 9G 8G 7G lC 9G

~2Z;~:74'7 Te~e B
Two 25 cm diameter pla~tic container6 were lined with pla~tic bags and filled wieh limed ~ood~town 6andy loam. A 25 cm diameter acrylic planting tem-plate wa~ u6ed to 61ightly compre66 the 60il withineach container and to provide indentation6 for the planting of nine te6t 6pecies. Seed6 of the following 6pecies were placed in one cvn~ainer: cocklebur (Xanthium pen6ylva~nicum), velvetleaf (Abutilon theo-Phca6ti), 6ugar beet6 (Beta vulaaris3, 6i~klepod(Ca66ia obtu~ifolia), morningglory (IPomoea 6pp.), ~eaweed (Sida 6Pinosa), coteon (Go66vPium hir6utum), jim60nweed ~Datura ~tramonium) and Goybean ~Glvcine max.). The 6econd pot ~a~ planted with seeds or tuber~ of the following 6pecie6: purple nut6edge (CYPeru~ rotundu6), rice (OrYza 6ativa), giant foxtail (Setaria faberii), crabgra66 (Diaitaria ~anquinali6), john60ngra66 (Sor~hum halePen~e), wild oat~ (Avena - fatua), w~eat (Tciticum ae6tivum), barnyardgra~6 (Echinoc~loa cru~qalli), and corn (Zea maY6). Both containers were then topped witb an approximately 1 cm layer of 60il to cover the 6eed6. The6e two container6 were then ~prayed preemergence with 6everal te6t compound~ from within the 6cope of the invention.
Following treatment, ~e planting6 leceived approxi-mately 1 cm of ~imulated rainfall in a period of 150 minute6.
Approximately twenty-eight day~ after treatment, the plant6 were vi6ually rated for re6pon6e to the chemical treatments utili2in~ the rating 6ystem previou61y de6cribed for Te6t A. Re~ult6 are pre6en~ed in Table B.

Table B

Compound 2 Rate kg/ha 1/161/10241/256 1/41/64 Rice lOC7G 9G lOClOC
Barnyardgrass 9G 2G 5G 9G 8G
Wheat 3G O Q 8G O
~ild Oats 9G 3G 6G 9G8G
Crabgrass 7G O 3G 9G4G
Johnsongrass 9G 2G 2G 9G BG
10 Giane Foxtail BG 2G 2G 9G 7G
Corn lOC O 6G lOC9G
Cocklebur 9G 2G 4G 9G7G
Nutsedge 9G O 4G lOC9G
Cotto~ 9G O 4G 9G8G
Morningglory 9G O 5G 9G 8G
Sicklepod 9G O 3G 9G8G
Teaweed 9G O 3G 9G7G
15 Velvetleaf 9G 4G 4G 9G7G
Jim60nweed 9G O 2G 9G8G
Soybean 9G O 2G 9G7G
Sugar beet lOC7G 9G lOClOC

.

1~8 Test C
In Test C, plastic pots filled with Fallsington sandy loam were planted to soybean6. cotton, corn, rice, wheat, sorghum, velvetleaf (Abutilon theo-phrasti), sesbania (Sesbania exal~ata), ca66ia (Cassiatora), morningglory (IPomoea spp.), jimsonweed (Datura stramonium), cocklebur (~anthium Pensylvanicu~m)~ crab-gra~6 (Dicitaria 6pp.), nutsedge (CYperufi rotundus), johnsongrass (Sor~hum halepense), barnyardgrass (Echinochloa crus~alli), giant foxtail (setar-i-a faberii) and wild oat~ (Avena fatua). Eighteen days after planting, the young plants and the soil around them were sprayed overall with the te6t chemical dissolved in a non-phytotoxic solvent. Fourteen days after treatment, all species were compared to untreated controls and visually rated for response to treatment utilizing the rating system previously described for Test A. The ratings for the compound tested by this procedure are presented in the Table C.

22~79LP7 Table C

ComPound 1 Rate kg/ha 1/64 1~4 1/256 1/16 Soybean 4C 9C O 9C
Corn lC lC O lC
Cotton 0 3C O 2C
Rice 0 4G O O
Wheat O O O O
Velvetleaf O lOC O 7G
10 Se6bania 5C 9G O 9G
Sicklepod lC 7G O 3C
Morningglory 0 3G O O
Jimsonweed 2G 4G 2G O
Cocklebur 7G lOC - lOC
Sugar beet9G BG 5G 8G
Crabgras~ O O O o Barnyardgrass 0 0 0 0 15 Giant Foxtail O O O O
Wild Oat~ O O O O
So~ghum 0 5G O 2C
Nutsedge O lC O O
Johnsongras~ O O O O

comPound ?
Rate kg/ha 1/64 1/4 Soybean 9G 9G
Corn lC ZC
Co~ton BG 7G
25 Rice O O
Wheat O O
Velvetleaf 8G 8G
Sesbania 9G 8G
Sicklepod ~C 4G
Morningglory 6G 3G
Jimsonweed - 3G
Cocklebur lOG lOG
30 Sugar beet lOC lOC
Crabgrass 0 3G
Barnyardgras6 0 0 Giant Foxtail 0 2G
~ild Oats 0 lG
Sorghum - -Nutsedge 6G 5G
35 John~ongra66 0 o ~2;~7~

Test D
-Sixteen-cm diameter glazed clay ~agner pot~, e~uipped with a 6toppered drain opening near the bottom of the ~ide wall, were partially filled with Woodstown ~andy loam~ About 1500 ml of water were added to each pot to bring the water level to a point 3 cm above the soil surface. Also, a number of barn-yardgrass (Echinochloa crusqalli~ seeds were added to each pot. At the same time, seedling6 or tubers of the following species were tran6planted into the muddy 60il: water plantain (Alisma trivale), Scirpus (Scir-PU8 mucranatus), and Cyperu6 (CYPeru6 difformi_). The weed species ~elected for thi6 test are of economic importance in major rice-growing area6. The chemial treatments were applied as de6cribed below in the crop response portion of the test within hour after trans-planting of two additional species: water che6tnut (Eleochari6 6pp. ) and arrowhead (Saqittaria latifolia).
Shortly after treatment, the drain hole was opened to drop the water level by two cm. Water was then added to res~ore the water level to it6 original height.
The following day the draining and refilling process was re~eated. The pots were then maintained in the greenhou~e. Rates of application and plant re~ponse ratings made 21 days after treatment are summari7ed in Table D.
In the crop re~ponse portion, twelve-cm diame~er waxed paper cup6 were partially filled with ~oodstown sandy loam. About 750 ml of water was added to each cup to bring the water level to a point 3 cm above the ~oil fiurface. Japonica rice seed was added to the pots, ~he 6eeds coming to re~t on the 60il surface (direct ~eeded rice). In addition, Japonica rice seedling6 in ~he 2.5 leaf 6tage were tran6planted into ~he same pots. Five days after seeding and ~ ~ A ~J

tran6planting compound number 1. di6solved in a small volume of acetone, wa6 injected into the water of the simula~ed rice paddy. The rate6 of application and the crop re6pon~e ratings made 10 day~ after treatment are ~hown in Table D.

Table D

Rate gm/ha 8 2 Barnyardgras~ 60 30 ~ater Chestnut 20 o Arrowhead 100 80 Sciepu6 70 100 Cyperus 100 100 Water plantain 90 0 Crop Response Transplanting Direct Seeded gm~ha 0063 40 g 0004 20 o 25 .25 10 o

Claims (24)

WHAT IS CLAIMED IS: BA-8591-A

1. A compound of the formula I
wherein Q is or ;

W1 is O or S;
R7 is H or CH3:
R is H, C1-C4 alkyl optionally substituted with 0-3 halogen atoms selected from 1-3 F, 1-2 Cl or 1 Br, C1-C4 alkylthio, C1-C4 alkoxy, CH2OCH3. CH2CH2OCH3 or CH2SCH3;
R1 is H, halogen, C1-C3 alkyl, C1-C3 haloalkyl, nitro, C1-C3 alkoxy, di(C1-C2)alkylamino-sulfamoyl, C1-C3 alkylthio, C1-C3 haloalkoxy, C1-C3 haloalkylthio, cyano, C1-C3 alkylsul-finyl, C1-C3 alkylsulfonyl, C2-C3 alkoxycar-bonyl, CH2OCH3, CH2SCH3 or CH2CN:
R2 is H or CH3:

W is O, S or NR3;
R3 is H or CH3 A is X is H, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 halo-alkoxy, C1-C3 haloalkyl, C1-C3 haloalkylthio, C1-C3 alkylthio, halogen, C2-C3 alkoxyalkyl, C2-C3 alkoxyalkoxy, amino, C1-C3 alkylamino or di(C1-C3)alkylamino;
Y is H, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 halo-alkoxy, C1-C3 haloalkylthio, C1-C3 alkylthio, halogen, C2-C3 alkoxyalkyl, C2-C3 alkoxyalkoxy, amino, C1-C3 alkylamino, di(C1-C3)alkylamino, C3 alkenyloxy, C3 alkynyloxy, C2-C3 alkynyl, C2-C3 alkylthioalkyl, C2-C3 alkylsulfinyl-alkyl, C2-C3 alkylsulfonylalkyl, C1-C3 halo-alkyl, cyclopropyl, C(O)R4, or N(OCH3)CH3:

m is 2 or 3;
L1 and L2 are independently O or S;
R4 is H or CH3;
R5 and R6 are independently C1-C2 alkyl:
Z is CH or N;
Y1 is O or CH2:
X1 is CH3, OCH3, OC2H5 or OCF2H;
Y2 is H or CH3:
X2 is CH3, OCH3 or SCH3;
Y3 is CH3, C2H5 or CH2CF3;
X3 is CH3 or OCH3;
X4 is CH3, OCH3, OC2H5, CH2OCH3 or Cl; and Y4 is CH3, OCH3, OC2H5 or Cl;
and their agriculturally suitable salts;
provided that a) when W1 is S, then R7 is H, A is A-1 and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3, CH(OCH3)2 or ;

b) when X or Y is OCF2H, then Z is CH;
c) when X is F, Cl, Br or I, then Z is CH and Y
is OCH3, OC2H5, OCF2H, NH2, NHCH3, N(OCH3)CH3 or N(CH3)2;
d) when R1 is di(C1-C2)alkylaminosulfamoyl or C2-C3 alkoxycarbonyl, then Q is Q-1 and R1 is in the 5-position; or Q is Q-2 and R1 is in the 6-position; and e) when the total number of carbon atoms of X
and Y is greater than four, then the number of carbon atoms of R is less than or equal to two, and the number of carbon atoms of R1 is less than or equal to two.

2. The compounds of Claim 1 whete W1 is O, R7 is H, X is CH3, OCH3, OC2H5, halogen, OCF2H, CH2F, OCH2CH2F, OCH2CHF2, OCH2CF3 or CF3, and Y is H, CH3, OCH3, OC2H5, CH2OCH3, NHCH3, N(OCH3)CH3, N(CH)2, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, C?CH, C?CCH3, CH2OC2H5, OCH2CHOCH3, CH2SCH3, C(O)R4, SCF2H or cyclopropyl.

3. The compoundS of Claim 2 where R1 is H, F, Cl, Br, CH3, OCH3, OCF2H, CF3, CH2OCH3 or CH2SCH3, R is H or C1-C2 alkyl, and Q is Q-1 or Q-2.

4. The compounds of Claim 3 where A is A-1, X is CH3, OCH3, Cl, Br or OCF2H, and Y is CH3, OCH3, CH2OCH3, NHCH3. C2H5, CH(OCH3)2. cyclopropyl, C?CH
or C?CCH3.

5. The compounds of Claim 4 where Q is Q-1 and R1 is H.

6. The compounds of Claim 4 where Q is Q-2 and R1 is H.

7. The compounds of Claim 5 where W is O.

8. The compounds of Claim 5 where W is S.

9. The compounds of Claim 5 where W is NR3.

10. The compounds of Claim 6 where W is O.

11. The compounds of Claim 6 where W is S.

12. The compounds of Claim 6 where W is NR3.

13. The compound of Claim 1 that is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methylbenzo-thiazole-4-sulfonamide.

14. The compound of Claim 1 that is N-[(4-methoxy-6-methyltriazin-2-yl)aminocarbonyl]-2-methyl-benzothiazole-4-sulfonamide.

15. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 1.

16. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 2.

17. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 3.

18. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 4.

19. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 5.

20. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 6.

21. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 7.

22. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 8.

23. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 13.

24. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 14.